The year 2026 is absolutely groundbreaking for Chicago USA, and it’s worth adding to your travel bucket list because the city is buzzing with incredible energy right now. Not only did the magnificent Obama Presidential Center open its doors on June 19, 2026, but the legendary Route 66 is celebrating its 100th anniversary this year. National celebrations kicked off on April 30, and the city has become the main pilgrimage destination for fans of this iconic highway.
Chicago USA is considered by many travelers to be the best American destination for architecture lovers, and it will instantly impress you with its grandeur. Everything essential is located in the compact downtown area called the Loop or along Lake Michigan, so you can easily get around on foot. While the city has a reputation for being dangerous, the tourist reality is completely different, and if you follow basic safety rules like traveling in fuller metro cars after dark, you have absolutely nothing to worry about.
Before you start planning your budget, I need to warn you about an important practical matter regarding costs. Since this spring, Chicago has had the highest hotel tax in the entire United States, which climbs up to 19% in the city center. On top of that, a Tourism Improvement District fee was added starting May 1, 2026, so carefully check the final amount when booking accommodation so you’re not unpleasantly surprised at checkout. Before your trip, don’t forget to arrange your ESTA to the USA: how to complete the application step by step well in advance, as you won’t be allowed on the plane without it. ☺️
TL;DR
- Best experience: An architecture boat tour on the river is an absolute must that tour guides and all locals unanimously agree on.
- Beautiful views: Skydeck Chicago in Willis Tower offers glass boxes called The Ledge, while 360 CHICAGO features the adrenaline-pumping tilting TILT.
- Top-notch museums: Don’t miss the Field Museum with the stunning T-Rex skeleton SUE and the magnificent Art Institute of Chicago.
- 2026 novelty: The newly opened Obama Presidential Center in Jackson Park requires timed tickets booked well in advance.
- Big anniversary: Get your photo at the iconic Begin Route 66 sign on Adams Street, celebrating its 100th anniversary this year.
- Affordable transportation: An all-day public transit pass for $5 pays for itself after just two rides; from O’Hare Airport you can take the Blue Line directly to downtown.
- Excellent dining: Try the famous veggie deep-dish pizza and visit the legendary vegetarian restaurant The Chicago Diner.
The full destination guide: USA Travel Guide — guide and what to see
When to Visit Chicago
Weather plays an absolutely crucial role when planning a visit to this windy city, because the extremes here can be truly unpleasant. If you can, head here in May, June, or September and early October, when you’ll be greeted by pleasant temperatures and beautifully sunny skies. The city comes alive outdoors during these months, local parks are in full bloom, and all the popular architecture boat tours on the river are running. Plus, you won’t be suffocating in summer heat during this period, so long walks along the promenade by the massive lake are simply perfect.
On the other hand, give the winter months a wide berth unless you’re a hardcore cold-weather enthusiast who enjoys freezing adventures. In January, temperatures commonly drop to around 14°F (-10°C), and the notorious icy wind from Lake Michigan makes the feels-like temperature even worse. The streets are nearly impossible to walk in winter, and you’ll be grateful for every open shop where you can take shelter. The only advantage of winter is that museums and galleries are completely empty, so you’ll have famous paintings and dinosaur skeletons all to yourself.
July and August bring temperatures around 86°F (30°C) with very high humidity, which can be quite exhausting among the glass skyscrapers. A huge advantage of August, however, is that you can actually swim in the lake’s waves and cool off. The water in Lake Michigan warms up to a pleasant 68–72°F (20–22°C) by late summer, transforming the city into a genuine beach destination full of sunbathers.
Where to Stay in Chicago
The best base for comfortable city exploration is downtown itself, called the Loop, or the neighboring modern River North district. You’ll be close to most attractions, and these are very safe tourist areas where you can move around without worry even after dark. While the Loop is more business-oriented and close to museums, River North offers a more varied nightlife and plenty of excellent restaurants. This is where you should prepare for the aforementioned 19% hotel tax, which you’ll only see at final checkout, so factor it into your budget in advance. You can find more detailed information in our article Where to Stay in Chicago.
If you’re looking for absolute luxury with impeccable service, definitely check out The Langham, Chicago, which is housed in a beautiful modernist building and offers absolutely breathtaking views directly over the river. For an excellent price-to-quality ratio downtown, I recommend the very popular Hyatt Regency Chicago, from which you can walk to Millennium Park in just a few minutes at a leisurely pace. If you have a smaller budget and are looking for stylish boutique accommodation, an excellent choice is Freehand Chicago, which is located just steps from the famous Magnificent Mile shopping street. Always book in advance through Booking, because in high season the best spots disappear in a flash. 😉
From a safety perspective, it’s good to know that violent crime is concentrated in outlying neighborhoods on the south and west sides, where you won’t venture as a typical tourist and have no reason to go. Still, it pays to use common sense. On the metro after dark, always sit in a car with more people and don’t unnecessarily hold your phone in your hand right by the doors when the train is stopping at a station. From O’Hare International Airport, you can get downtown safely and quickly via the CTA Blue Line in about 45 minutes, which thanks to heavy traffic is often faster than an expensive taxi.
💡 On this map you can compare what’s currently available — you’ll immediately see how much cheaper a hotel two stops from the Loop is.
22 Things to See and Do in Chicago
Let’s take a look together at the very best this iconic American city has to offer. I’ve prepared for you exactly 22 specific tips on places and experiences that you definitely shouldn’t miss during your visit, whether you’re coming for architecture, history, or great food.
1. Millennium Park and the Famous “Bean”
Your exploration of the city should begin right in Millennium Park, which is the most visited place in all of Chicago and the pulsing heart of the metropolis. The main draw is undoubtedly the giant mirrored sculpture Cloud Gate, which everyone calls simply the Bean, and which has become the city’s modern-day symbol. Its stainless steel surface perfectly reflects the surrounding skyscrapers and sky, creating absolutely fantastic opportunities for original photographs. Try to arrive early in the morning to avoid the biggest crowds and have the sculpture to yourself, at least for a moment.
Just a short distance away, you’ll find the fascinating Crown Fountain, formed by two glass towers on which giant faces of local residents are projected. At regular intervals, water shoots from the mouths of these digital faces, which children and adventurous adults especially love during hot summer months. The entire park is a showcase of excellent modern architecture, and admission is completely free, which is a very pleasant bonus in the rather expensive downtown area.
Also worth your attention is the imposing Jay Pritzker Pavilion designed by renowned architect Frank Gehry, which from a distance resembles a giant blooming metal flower. Its popularity is evidenced by tens of thousands of positive Google reviews. During the summer season, free concerts and film screenings are held here, so all you need to do is bring a blanket, buy some good food, and enjoy the evening like a true local. 💡 Tip: The park flows seamlessly into Maggie Daley Park, where you’ll find a great roller skating track and in winter, magical ice skating.
2. Chicago Riverwalk
If you want to experience the city from a completely different perspective, head to the Chicago Riverwalk, a stunning pedestrian promenade that lines both banks of the river right in the heart of the skyscrapers. It’s a place where history blends with modern lifestyle, and you’ll find plenty of inviting bars, cafés, and relaxation zones. You’re literally walking through a fascinating canyon of steel and glass. Especially in the early evening, when the city starts to light up, a stroll along the water has an absolutely unforgettable romantic atmosphere.
The promenade is divided into several themed sections, each offering a slightly different experience, from quiet nooks to bustling restaurants with live music. You can sit down on steps right at the water’s edge and watch passing boats and water taxis glide by, or even rent a kayak yourself and explore the city on your own. It’s an absolutely fantastic way to escape the noise from the busy streets above you.
💡 Tip: Most of the sightseeing boats depart right from here, so it’s the ideal spot to combine a pleasant walk with another item on your itinerary. I recommend grabbing a coffee to go from one of the many cafés and enjoying the views of passing boats right from a bench by the water.
3. Architectural River Cruise
If there’s one experience in Chicago you absolutely shouldn’t miss, it’s the architectural river cruise, which absolutely everyone agrees on. This roughly 90-minute boat tour is the very best introduction to the city, as it perfectly presents its rich history and urban development. The best-rated cruises are organized by the official Chicago Architecture Center, whose guides are very often passionate volunteers who tell the stories of the buildings with tremendous enthusiasm.
During the cruise you’ll travel right through the city center, and from the boat deck you’ll get the best angle for photographing the iconic skyscrapers. The guides will explain in detail how the city recovered from the Great Fire and how it became the worldwide cradle of modern architecture that we still admire with bated breath today. You’ll discover how architectural styles evolved from heavy masonry to modern glass towers.
💡 Tip: Book tickets for a sunset cruise, when the building façades are bathed in golden light and the cruise experience is absolutely magical. ☺️ During the summer months these evening times sell out far in advance, so definitely don’t delay booking online.
4. Skydeck Chicago at Willis Tower
For the most iconic bird’s eye view of the city, you need to head up to Skydeck Chicago, located on the 103rd floor of the famous Willis Tower. This building, which many locals still stubbornly call by its original name Sears Tower, held the title of world’s tallest building for many years. A standard ticket costs $32 USD for adults and $24 USD for children aged 3 to 11, while the very youngest get in completely free.
The main draw of this observation deck is an attraction called The Ledge, which consists of unique glass boxes extended out from the building, where you literally stand suspended in the air above the streets. It’s quite an adrenaline-pumping experience to look directly down at your feet and see yellow cabs like tiny ants more than 400 meters below you. When else will you get the chance to levitate this high above one of America’s greatest cities?
💡 Tip: Be prepared for long lines at the glass boxes, so arm yourself with patience. The absolute best strategy is to reserve a time slot right at the first morning opening time, when it’s pleasantly quiet and you won’t have to wait dozens of minutes for photos in the glass box.
5. 360 CHICAGO and Adrenaline-Pumping TILT
While from Willis Tower you see mainly the enormous sprawl of the city, the observation deck at 360 CHICAGO on the 94th floor of 875 North Michigan Avenue offers what many consider a much more beautiful view of the actual skyline. This building, formerly known as the John Hancock Center, sits right by the lake, so you have the iconic skyscrapers and the blue expanse of Lake Michigan in the palm of your hand. This is where you’ll capture the most classic postcard photos of the entire city, because from this distance you can even see Willis Tower itself.
If you’re not short on courage, definitely try the local attraction TILT, which has no equivalent anywhere in the world. It’s a special movable glass wall that you stand against, hold firmly onto the handles, and the entire mechanism slowly tilts you outward over the busy street at a 30-degree angle. It’s a strange feeling when only thick glass separates you from free fall.
💡 Tip: This observation deck has an excellent bar called CloudBar, so you can buy your favorite drink, sit by the window, and savor the sunset with a cocktail in hand. It’s an absolutely fantastic and very relaxing experience after a full day of walking.
6. Art Institute of Chicago
Art lovers have an absolutely clear destination in Chicago, which is the Art Institute of Chicago, by far the best-rated museum in the city with tens of thousands of enthusiastic reviews. This enormous institution holds one of the finest art collections in the entire world and you can easily spend a whole day here without getting bored for even a second. A standard ticket for non-residents costs $32 USD, while seniors and students get discounted admission for around $26 USD.
Among the biggest highlights are legendary paintings you know from history textbooks, including the famous canvas Nighthawks by Edward Hopper and the iconic American Gothic by Grant Wood. The museum also boasts the largest collection of Impressionist works outside Paris, so here you’ll see with your own eyes the stunning Seurat masterpiece A Sunday Afternoon on the Island of La Grande Jatte, composed of millions of tiny dots.
💡 Tip: Don’t forget to visit the modern wing designed by renowned architect Renzo Piano, which is itself an architectural gem. From this wing you can also reach Millennium Park via a special bridge, which offers beautiful views of the city skyline.
7. Chicago Cultural Center
If you’re looking for a magnificent experience that won’t burden your travel budget at all, you absolutely must not miss the Chicago Cultural Center, which is the best hidden gem in the entire Loop. This majestic building originally served as the main city library and its interiors showcase absolutely incredible craftsmanship and luxury. The enormous marble staircase and rich mosaics on the walls instantly transport you to the golden age of American prosperity.
But the most beautiful treasure of the entire building is the world’s largest stained glass dome by the famous Tiffany studio, which majestically adorns one of the halls on the upper floor. The sight of daylight passing through thousands of tiny colored glass pieces is truly magical. And what’s best of all, admission to the entire building is completely free, making it an ideal stop for warming up in winter or cooling down in summer.
💡 Tip: Check the current program on the official website, because they regularly host free concerts, interesting exhibitions, and cultural events for the public. You can easily just sit here with a book and enjoy the fantastic historical atmosphere in complete peace.
8. Field Museum and T-Rex SUE
When you head a short distance south to the beautiful Museum Campus area, your first stop should be the phenomenal Field Museum, which is a dream come true for all natural history enthusiasts. Right in the main grand hall you’ll be greeted by Máximo, the largest discovered titanosaur in the world, who is so gigantic that he barely fits in a single camera frame. The museum is absolutely fantastic for families with children, but its elaborate exhibitions will reliably captivate adult travelers as well.
But the absolute biggest celebrity of the entire museum is undoubtedly SUE, which is the most complete and best-preserved T-Rex skeleton on our planet. SUE even has her own specially lit exhibition, where you’ll learn fascinating details about the life of this prehistoric predator and see her original, incredibly heavy skull displayed separately.
💡 Tip: The museum is truly gigantic and requires a lot of walking, so wear your most comfortable shoes and set aside at least three to four hours minimum for the visit. If you want to see special 3D films and temporary exhibitions as well, it’s worth buying the comprehensive All-Access Pass.
9. Shedd Aquarium
Right next to the natural history museum in the Museum Campus area you’ll find Shedd Aquarium, which undoubtedly ranks among the very largest and most respected aquariums in the entire USA. It’s housed in a beautiful historic building with classical columns right on the lakeshore and inside it houses an incredible diversity of aquatic life from all corners of the world. From vibrant coral reefs teeming with life to the cold waters of the Pacific Northwest, all the exhibitions are designed with tremendous attention to detail.
You can look forward to playful beluga whales, elegant dolphins, adorable sea otters, and fascinating sharks that silently swim in enormous glass tanks right above your heads. The aquarium places great emphasis on nature conservation and during regular presentations you’ll learn lots of interesting information about saving fragile marine ecosystems.
💡 Tip: Definitely buy tickets online well in advance, because during summer months, weekends, and holidays the best time slots sell out very quickly. Lines at the ticket counters can be endless, and buying tickets in advance will save you loads of precious time.
10. Adler Planetarium and the Best Free View
The trio of major institutions at Museum Campus is proudly completed by Adler Planetarium, which sits at the very end of a peninsula jutting into Lake Michigan. The planetarium itself offers excellent interactive exhibitions about space exploration and state-of-the-art star projections in a giant dome that literally immerse you in the depths of space. It’s an absolutely ideal place for anyone who loves stargazing and is fascinated by the history of the American space program.
But the main charm of this place for the average tourist lies outside, because from the planetarium terrace you get the absolute best view of the Chicago skyline. You’ll see the entire wall of skyscrapers reflected on the water’s surface. And the best part? This breathtaking view is completely free – you don’t have to pay any admission, just walk along the promenade to the end and enjoy the view to the fullest.
💡 Tip: Head here in the early evening with a picnic blanket, sit on the grass, and watch as the skyscrapers gradually light up against the darkening sky. It’s one of the most romantic and photogenic moments you can experience here.
11. Griffin Museum of Science and Industry
If we had to choose the most fun museum in the city, the clear winner would be Griffin Museum of Science and Industry, located a bit further south in Jackson Park. It’s a huge interactive playground where the rule is that you absolutely must touch the exhibits, which makes it the very best museum for families with children in the entire United States. The building itself is a beautiful remnant of the famous World’s Fair of 1893.
Among the most unique exhibits is a real German U-505 submarine from World War II, which you can tour inside and experience the cramped atmosphere firsthand. Another huge hit is a working coal mine replica where you descend in a dark mine elevator, or the giant and incredibly detailed model railroad crossing all of America from coast to coast.
💡 Tip: For the U-505 submarine tour you need a special timed ticket, which you should buy right at the main entrance or online in advance to secure your spot. The tour is guided and the submarine’s capacity is very strictly limited.
12. New Obama Presidential Center
The year 2026 brought the city one of the biggest events of the last decade, which is the long-awaited opening of Obama Presidential Center. This magnificent complex welcomed its first visitors on June 19, 2026 on the symbolic Juneteenth holiday and immediately became a huge nationwide sensation. You’ll find it in historic Jackson Park on the south side of the city, which you can easily reach by Metra commuter rail or local CTA buses.
The main landmark of the entire complex is an imposing modern museum tower that innovatively tells the story of the first African American president and his challenging journey to the White House. The center also includes an extensive modern library, community spaces, and beautiful public gardens that seamlessly and sensitively blend with the surrounding greenery. It’s not just a dry museum full of display cases, but rather a vibrant space full of interactive exhibitions that draw you into recent American history and inspire civic engagement.
💡 Tip: Given the enormous interest from travelers worldwide, it’s absolutely essential to reserve timed tickets well in advance. The complex also offers great children’s playgrounds and outdoor trails, so for the visit set aside a good half day and combine it with a walk around the nearby historic campus.
13. Begin Route 66 Sign
Did you know that the famous Mother Road, the legendary Route 66, starts right here in Chicago? This iconic cross-country route this year celebrates an incredible 100 years since its creation and national celebrations kicked off in grand style on April 30, 2026. Exactly one hundred years since the road received its magical number, the city became the main hub of celebrations and an absolute pilgrimage site for road trip enthusiasts from around the world.
The official start of the route itself can be found at the rather unassuming intersection of Adams Street and Michigan Avenue right in the bustling downtown. There’s a famous brown sign reading Begin Route 66 where you simply must take a photo for the memories. There’s often a small line of enthusiastic travelers, but the wait is definitely worth it because a photo at this sign is the perfect and authentic travel souvenir.
💡 Tip: If the history of this road fascinates you, stop by local visitor centers for special commemorative maps that were released for this year’s big anniversary. You can also walk the first few blocks along Adams Street and soak up the atmosphere of the place from which entire generations of Americans set out for adventure to the sunny west.
14. The Loop and the Birthplace of Skyscrapers
Architecture lovers will find heaven in Chicago because the Loop downtown serves as a fascinating open-air architecture gallery. The city is rightfully considered the true birthplace of skyscrapers and you’ll find buildings here that forever changed the face of world metropolises. Just walk with your head up and admire the details that old buildings offer at every turn.
Don’t miss the iconic Rookery Building with its breathtaking light court, whose ground-floor design was refined by none other than the legendary Frank Lloyd Wright himself. Nearby stands the massive Monadnock Building, which with its incredibly thick walls is the tallest building with load-bearing brick walls in the world. You’ll also see the gorgeous neo-Gothic Tribune Tower studded with stones from around the globe, or the iconic Chicago Board of Trade building in art deco style.
💡 Tip: Besides the old classics, admire modern gems like Marina City, playfully nicknamed the corn cobs for their shape, or the elegant undulating Aqua Tower, which ranks among the most photographed contemporary buildings anywhere.
15. Navy Pier
If you’re looking for a place full of relaxed fun and attractions, head to Navy Pier, a massive pier stretching far out into the waters of Lake Michigan. I’ll honestly admit it’s quite a touristy spot full of stalls and loud music, but families with children especially will have a great time and spend a wonderful afternoon full of laughter. From the pier you get beautiful views of the city and the endless water surface that feels more like the ocean than a lake.
The pier’s main landmark is the giant Ferris wheel Centennial Wheel, which operates year-round because its cabins are safely enclosed, air-conditioned and heated. You’ll also find a huge children’s museum, the beautiful indoor Crystal Gardens conservatory, and plenty of quick-service restaurants.
💡 Tip: In summer months, spectacular fireworks displays are regularly held here, best viewed from a sightseeing boat or right from the promenade on the pier, so plan your visit for evening hours and combine it with a romantic walk.
16. Lincoln Park and Free Zoo
When you want to escape the hustle and bustle of the big city, head north to the Lincoln Park neighborhood, considered the best walkable urban area in the city. You’ll find beautiful tree-lined streets, historic brick houses, and most importantly a huge park of the same name that serves as the green lungs of all Chicago. It’s the perfect place for a peaceful walk with coffee in hand while admiring the local laid-back atmosphere.
Inside the park sits the popular Lincoln Park Zoo, one of the last major zoological gardens in the USA with completely free admission. You can stroll completely free among lion, monkey and giraffe enclosures, while modern skyscrapers rise in the background, creating an amazing visual contrast between wild nature and concrete.
💡 Tip: Right next to the zoo you’ll find the beautiful Lincoln Park Conservatory greenhouse, which is also free and offers a tropical oasis full of exotic plants, ferns and soothing fountains where locals love to escape from harsh weather.
17. Wicker Park and Bucktown
If you’re drawn to alternative culture and an artistic atmosphere, hop on the blue metro line and head to the neighboring districts of Wicker Park and Bucktown. These areas northwest of downtown are the heart of Chicago’s hipster scene and offer an incredible array of independent boutiques, vinyl record shops and excellent thrift stores. It’s where locals spend weekends shopping and hanging out with friends at outdoor patios.
The streets are full of life and you’ll find hands down the best and most stylish coffee shops in the entire city, where local baristas will prepare specialty coffee in a hundred different ways. In the evening the whole neighborhood transforms into a lively nightlife hub with plenty of great cocktail bars and small clubs featuring live music.
💡 Tip: Walk down the main artery Milwaukee Avenue, which is the beating heart of the whole district and where you’ll reliably hunt down the most interesting souvenirs and original vintage wardrobe pieces at very reasonable prices. 😅
18. Pilsen and Mexican Culture
For street art lovers and authentic culture seekers, the Pilsen neighborhood is an absolute must that will instantly charm you with its vibrant colors. This originally Czech neighborhood, as its name clearly suggests, has over the years transformed into a pulsating center of Mexican culture and community, which is reflected in the local unmistakable atmosphere at every turn. Building walls are adorned with dozens of beautiful and elaborate murals that tell stories about the history, hopes and struggles of local residents.
The main attraction of this neighborhood is undoubtedly the National Museum of Mexican Art, which has completely free admission and houses one of the largest collections of Mexican art in the entire United States. You can admire everything from traditional textiles to modern paintings by Mexican artists.
💡 Tip: Come here for excellent authentic tacos for lunch and walk especially along 16th Street. That’s where you’ll find along the old railroad embankments the greatest concentration of street art in one place, which is absolutely ideal for lovers of colorful and original photography.
19. Chinatown and Asian Flavors
Chicago proudly boasts one of the largest Asian communities in the USA and the local Chinatown neighborhood is an absolutely excellent place for an afternoon of exploration and shopping. Right when you exit the CTA red line metro you’re greeted by a richly decorated entrance gate and bustling streets full of aromas from dozens of authentic restaurants and traditional bakeries. The atmosphere here is utterly immersive, you’ll see plenty of traditional herb shops and prices are often much friendlier than in the very center of the city.
The neighborhood is divided into an old historic section and the newer Chinatown Square, which is full of modern bistros and bubble tea shops. If you’re looking for excellent plant-based food, local establishments like Veggie House or Vegan Plate offer fantastic Asian specialties in purely vegan versions.
💡 Tip: Go for traditional dim sum, or visit the wonderful Ping Tom Memorial Park. It features a charming traditional-style pagoda and offers a beautiful view of skyscrapers and passing water taxis, making it a great spot to rest after a long walk.
20. Montrose Beach and Swimming in the Lake
It might surprise you a bit, but Chicago in summer is a full-fledged beach destination where people come to relax with genuine joy. Along the entire shoreline stretches a network of groomed city beaches, with the most popular being the northern Montrose Beach. It offers beautifully fine sand, very good facilities and a huge area, so crowds easily spread out. In August thousands of people regularly swim here because the water in vast Lake Michigan reaches a pleasant 20–22 °C (68–72 °F).
The view from the beach across the open water surface with no opposite shore easily gives you the feeling you’re swimming in the ocean rather than a lake. There are also beach volleyball courts available and refreshment stands.
💡 Tip: Rent a shared Divvy bike for a few dollars and ride along the 18-mile-long Lakefront Trail that seamlessly connects all the beaches. From this route you’ll capture amazing photos with the city in the background while enjoying fresh air from the water.
21. Sports Madness at Wrigley Field
American professional sports are an inseparable part of the city, and Chicago fans are famous across the country for their incredible loyalty and passion. Even if you’re not a baseball fan, visiting the historic Wrigley Field stadium, home to the legendary Cubs, is an enormous cultural experience worth having at least once in your life. The stadium is absolutely iconic with its ivy-covered walls and sits in the middle of a lively neighborhood full of rowdy sports bars, aptly named Wrigleyville.
The atmosphere around the stadium on game day is absolutely electrifying, with streets packed with people in blue jerseys and loud music blasting from the bars. If you can’t manage to get tickets to the actual game, just grab a seat in one of the surrounding establishments and soak up that genuine American sports energy.
💡 Tip: If you’re visiting outside the main season, don’t despair. You can pay for an official guided tour of the stadium and see behind the scenes, into the locker rooms, and right onto the field—places you normally wouldn’t access at all—and learn everything about the club’s rich history.
22. Try the Local Food Legends
The gastronomy scene here is world-famous, and the local culinary specialty number one is undoubtedly the massive deep-dish pizza. This treat with a high crust, loads of cheese, and thick tomato sauce is traditionally baked with sausage, but veggie deep-dish pizza is absolutely standard in the city, so you can enjoy it perfectly in a vegetarian version too. Likewise, the legendary Chicago hot dog, which is strictly served without ketchup, now has an excellent plant-based “veggie dog” variant at many places.
If you’re looking for a guaranteed plant-based option in a relaxed setting, head to the beloved institution The Chicago Diner in the Lakeview neighborhood. This restaurant has been operating since 1983 with the proud motto “Meat Free Since ’83” and became famous for its absolutely phenomenal vegan milkshakes, which regularly draw long lines. Another excellent choice is the modern PLANTA Chicago restaurant in River North.
💡 Tip: Locals actually prefer what’s known as tavern-style pizza, which is, on the contrary, extremely thin, crispy, and cut into small squares. For a sweet finish, definitely grab Garrett Popcorn in the “Chicago mix” flavor, where sweet caramel and salty cheddar are mixed together.
Day Trips from Chicago
Once you’ve explored the city itself and want to see something more, head out for a trip to the surrounding area, which offers surprising diversity and beautiful nature. Just beyond the city limits lies peaceful Oak Park, which you can reach in just 25 minutes by train. You’ll find the world’s largest concentration of preserved buildings by Frank Lloyd Wright, including his own home, as well as the birthplace of the famous writer Ernest Hemingway.
If you’re drawn more to wild nature and an escape from concrete, hop on the South Shore Line train and in an hour you’ll be at Indiana Dunes National Park. This park will absolutely delight you with its enormous sand dunes that sit right on the lakeshore. Another beautiful and very popular natural stop is Starved Rock State Park with sandstone canyons and impressive waterfalls, located about two hours’ drive southwest.
For more American city sightseeing, you can head by comfortable Amtrak express train straight to Milwaukee. The journey takes just 90 minutes, and the city draws visitors with excellent local breweries and a stunning art museum by architect Santiago Calatrava. And since you’re at the very beginning of the legendary Mother Road, set off on Route 66 southward toward the towns of Joliet and Wilmington, where you’ll see the legendary Gemini Giant statue and experience genuine American nostalgia.
And if you’re planning a broader American road trip, definitely check out our other guides too:
Frequently Asked Questions
Is Chicago safe for tourists?
While the city has a reputation as a dangerous metropolis, for the average tourist this doesn’t match reality at all. Violent crime is concentrated in outlying neighborhoods on the south and west sides, where you have no reason to go. The Loop downtown, River North, the waterfront, and main attractions are safe—just on the metro after dark I recommend sitting in fuller cars and not holding your phone in your hand near the doors.
How many days should I set aside for a visit?
For the main highlights in the city itself, 3 full days will be more than enough, during which you’ll comfortably fit in museums, observation decks, and a river cruise. But if you want to visit the new Obama Presidential Center, explore the architecture in Oak Park, or head out to the sand dunes, ideally set aside 4 to 5 days.
When is the best time to visit?
You’ll find the best weather from May to June and then in September and early October. Temperatures are pleasant and you can spend lots of time outdoors along the lake. Definitely avoid January, when temperatures routinely drop to -10 °C and the icy wind off the lake makes walking around the city almost unbearable.
Should I choose Willis Tower or 360 CHICAGO?
It depends on what type of view you prefer. From the 360 CHICAGO observation deck you have the famous skyscrapers and enormous lake right at your fingertips, plus you can try the tilting attraction TILT. Willis Tower is higher and you can see farther inland, but you mostly see endless urban sprawl and the main draw is the glass boxes of The Ledge.
Is it worth buying the tourist CityPASS?
The CityPASS discount card is worth it for you only if you plan to visit at least three large and expensive institutions, such as Skydeck, Field Museum, and Art Institute of Chicago. If you want to pick just one or two attractions and spend the rest of your time exploring neighborhoods and parks, individual tickets will work out cheaper for you.
What about hotel tax and accommodation prices?
In 2026, the city has the highest hotel tax in all of the USA, which reaches up to an incredible 19% in the downtown area. On top of that, starting in May there’s also a Tourism Improvement District fee. When comparing prices online, always factor this in, because booking portals often show the base price without these massive surcharges.
How do I get from O’Hare Airport to downtown?
The best and fastest option is to take the CTA train Blue Line, which takes you straight into the Loop downtown. The journey takes about 45 minutes, a ticket costs a few dollars, and you avoid potential massive traffic jams in which an expensive taxi or Uber would definitely get stuck.
Tips and Tricks for Your Vacation
Don’t Overpay for Flights
Search for flights on Kayak. It’s our favorite search engine because it scans the websites of all airlines and always finds the cheapest connection.
Book Your Accommodation Smartly
The best experiences we’ve had when looking for accommodation (from Alaska to Morocco) are with Booking.com, where hotels, apartments, and entire houses are usually the cheapest and most widely available.
🚗 Car rental on the roadVerified rental cars in the United StatesSearch with the DiscoverCars comparison engine — it compares prices from dozens of local and international rental companies, and most bookings come with free cancellation.
Compare car prices in the United States →Don’t Forget Travel Insurance
Good travel insurance will protect you against illness, accidents, theft, or flight cancellations. We’ve had a few hospital visits abroad, so we know how important it is to have proper insurance arranged.
Where we insure ourselves: SafetyWing (simple monthly subscription) and TrueTraveller (for extra-long trips).
Find the Best Experiences
Get Your Guide is a huge online marketplace where you can book guided walks, trips, skip-the-line tickets, tours, and much more. We always find some extra fun there!
