20 Top Things to do in Chicago, Where to Stay, Dine and Explore
My Chicago travel guide has the top things to do in Chicago, the best places to stay in Chicago, restaurant recommendations and the best day trip ideas!
Did you know that Chicago has 24 sandy beaches? I sure didn’t! After years of wanting to visit, I finally made it to the Windy City, and it completely surprised me. I came expecting world-class architecture, renowned museums, and an eclectic music scene (which it delivered), but what truly impressed me were the 28 miles of lakefront, 8,800 acres of green space, and those unexpected stretches of beach. From sun-soaked shores to the iconic Bean, snazzy brunch spots to legendary Blues clubs, the top things to do in Chicago go far beyond the usual tourist checklist – this city is as dynamic as it is diverse.
About Chicago
Chicago, the third-largest city in the United States by both size and population, is a vibrant metropolis but also boasts a scenic location along Lake Michigan, offering plenty of opportunities for outdoor activities.
The city’s history is marked by the Great Chicago Fire of 1871, which devastated large sections of the city. However, the rebuilding efforts spurred rapid growth, attracting workers and fueling a construction boom. By 1900, Chicago had become the fifth-largest city in the world and gained international recognition for its innovative architecture, including the world’s first skyscraper built in 1885.
Today, more than 125 years later, Chicago is renowned for its world-class attractions, vibrant food scene, passionate sports culture, and its legacy as the blues capital of America. If you still need convincing – it has been voted the best big city in America 8 years in a row by readers of Condé Nast Traveler.
Summer is the best time to visit Chicago, with beaches, lakefront activities, and plenty of outdoor dining spots to take in those epic views. However, winters in Chicago can be very cold, with temperatures often dropping below zero, and with the added wind chill (there is a reason its called The Windy City), it can feel even colder.
Top things to do in Chicago
I’ve listed 20 top things to do in Chicago below, as well as hotel recommendations to suit all tastes and budgets. However, before you visit I suggest booking a CityPass which will save you up to 49% off 5 top Chicago attractions. I used this during my visit, and saved on the architecture cruise, 360 Skydeck and the Art Institute, but there are 8 different attractions to choose from. The app is very easy to use and you can reschedule times if necessary.
1. Explore Chicago’s River Walk
The Chicago Riverwalk is a 2km scenic promenade that stretches along the banks of the Chicago River. Lined with restaurants, bars, public art, and green spaces, the Riverwalk is the perfect place to go to on your first day in the city.
Stroll the promenade while taking in Chicago’s iconic architecture and stop for coffee, drinks or food in one of its many restaurants, beer and wine gardens, or grab a take away drink and chill on the many patios. I loved watching locals stroll or jog past me, it really felt like the heart of the city. You can also catch one of the many river cruises or kayaking trips along the river – see more on these below.
2. Walk Under The Bean
The Bean is a public sculpture located in Millennium Park in the heart of Downtown Chicago – it is a must see in Chicago! Officially titled Cloud Gate, it reflects the clouds above and the city’s famous skyline through its stainless steel exterior.
The Bean is 33 feet high, 42 feet wide, 66 feet long and weighs about 110 tons – it is one of Chicago’s most iconic sights. It is interactive too – you cant help but touch it and see your reflection all around you as you walk underneath it.
Fun fact: The Bean’s artist Anish Kapoor doesn’t title his works until they are completed, but when locals saw it being constructed they started calling the curved shape The Bean, and the nickname stuck!
3. Book an Architecture Cruise
An Architecture cruise is one of the top things to do in Chicago, and it is included as part of a CityPass. We did this on our first evening and it was a great introduction to the city. As well as enjoying a relaxing river cruise, the guided boat tour gave great insights into Chicago’s architectural history and the impact of the Great Fire.
Styles such as Art Deco, Modernism, and Postmodernism were highlighted over the 75 minute tour, but there were lots of surprises too! I loved seeing how the varying shades of blue glass give the illusion of curves in the St Regis – a building that not only has no curves, but is the tallest building in the world that was built by a woman.
The Willis Tower, formerly the Sears Tower, was the tallest building in the world for 20 years, but learning that this architectural marvel was designed to sway up to 3 feet in the wind, was even more fascinating! Chicago is the birthplace of the skyscraper and you will see and learn about plenty of them on this super tour.
4. Step onto the Ledge at Skydeck
Speaking of the Willis Tower, this is now home to Skydeck, America’s highest observation deck which is located on the 103rd floor. Step out onto the glass balconies – otherwise known as The Ledge, that extend out over the streets below, and take in the amazing views, that can span up to fifty miles away across four states! It’s a thrilling, one-of-a-kind way to take in Chicago’s skyline and one of Chicago’s top attractions.
However, the entrance ticket to Skydeck offers much more than an observation deck. On your way up, you will enjoy the Chicago Museum’s interactive experiences featuring the city’s history. Entrance is included on CityPass, or you can book separately, which I have linked below.
5. Take in the views from 360 Chicago
The John Hancock building offers another top Chicago attraction, 360 Chicago. This observation deck is located 1,030 feet above Chicago on the 94th floor. You can simply visit to take in the panoramic views, and enjoy cocktails from its popular Cloud Bar, or go one step further and try the TILT.
The TILT is a glass-panelled platform that leans 30° outward over Michigan Avenue. I did this, and while it is not for the faint hearted, it actually looks scarier than it is! It lasts only a few minutes, but it is a unique thing to do in Chicago and a must do for thrillseekers. Entrance to 360 Chicago (not TILT), is included with a CityPass, or you can book it separately, which is linked below.
6. Visit the Art Institute
The Art Institute of Chicago is not only regarded as the best museum to visit in Chicago, but it is one of the best art museums in the United States. It houses a world-class collection of art including Impressionist and Post-Impressionist masterpieces, including works by Monet and Van Gogh. Rotating exhibitions and interactive programs ensure there are plenty of interesting attractions to suit all tastes.
The building itself is stunning too, and it is one of the attractions included in the City Pass, so you can pop in at a time that is convenient to you. Alternatively book a private tour, which I have linked below.
7. Book the Bikes, Bites and Brews Tour – A Must Do in Chicago
Cycling in Chicago is a super way to explore the city, thanks to having 200 miles of bike lanes, paths and scenic routes. Don’t miss the picturesque Lakefront Trail, which stretches 18 miles along Lake Michigan and offers stunning views of the skyline and waterfront.
I can’t recommend the Bikes, Bites and Brews tour highly enough – this bike and food tour is one of the top things to do in Chicago. This not only takes in the Lakefront Trail and Lincoln Park, but also cycles through neighbourhoods that you would not ordinarily visit, with food and beer stops in some of Chicago’s iconic venues along the way.
We enjoyed delicious Deep Dish Pizza (more on this later), a famous Chicago hot dog, locally crafted beers, and a chocolate brownie ( the brownie recipe originated in Chicago), over four stops. The whole tour lasts 4.5 hours with four different food and drink stops along the way. It is remarkable value at $79 for a guided tour with food and drinks included.
Fun Fact: Did you know there are more hot dog vendors in Chicago than Mc Donalds, Burger King and Wendys combined?
8. Take in a game at Wrigley Field
Catching a game in Chicago is a quintessential experience for sports fans. We visited the historic Wrigley Field, home of Baseball’s Chicago Cubs. This stadium is known for classic neighbourhood setting that creates an intimate game-day atmosphere – CNN even voted it one of the 15 happiest places in the world!
You can also choose to cheer on the Bears at Soldier Field – the smallest American Football stadium in the NFL. Regardless of which game you choose, the energy and passion of Chicago fans is renowned across the US, and a vibrant atmosphere is guaranteed.
9. Walk the Magnificent Mile
The Magnificent Mile is Chicago’s top shopping street, with numerous designer brands, department stores and boutiques to tempt you. It is located on Michigan Avenue and there are plenty of cafés, bars and restaurants to relax in afterwards.
10. Enjoy complimentary concerts, movies or Yoga at Millennium Park
Millennium Park is not only home to The Bean, it is also home to countless activities, many of which are free of charge. The summer workout program takes place on the Great Lawn every Saturday with Pilates, Yoga, Kickboxing and Zumba taking place every 45 minutes from 8am.
Movies, free concerts and walking tours take place throughout the year too, you can see a full calendar of events below.
11. Catch the Fire Works at Navy Pier
Navy Pier is Chicago’s iconic waterside entertainment venue, which is home to a Ferris wheel, theme park rides, and plenty of dining options to suit all the family. The Flyover is its newest attraction, where you can soar over the streets of Chicago and through the world’s most iconic places in a simulator. Visiting Navy Pier is one of the top things to do in Chicago with kids.
Top Tip: Don’t miss the complimentary Fireworks display that takes place every Wednesday at 9pm and Saturday at 10pm from May 24th – August 30th. Navy Pier has been voted the best place to see fireworks for the past three years by USA Today! Make sure to get there 30 minutes in advance to get a viewing spot, and be prepared to walk back to your hotel or take the train afterwards, as taxis are not readily available.
12. Take the Kids to the Field Museum
The Field Museum is one of best museums in Chicago for families and dinosaur lovers. Also known as the Natural History museum, it is home to over 40 million artefacts including the famous T-REX named SUE, the largest and most complete Tyrannosaurus rex ever discovered.
The museum’s immersive displays make it engaging for visitors of all ages, and it is one of the top things to do in Chicago with children. Entrance is included with CityPass or you can purchase tickets separately here:
14. Kayak along the Chicago River
Kayaking along the Chicago River in a single or tandem kayak, for as little as €35, must be one of the most unique things to do in Chicago! You can even choose to extend your time and stop off at cafés and urban beachfronts. This activity is suitable for ages 13+ with adult supervision, and from 4+ if using a tandem kayak, so it is one of the top things to do in Chicago with kids.
13. Spend a day at the Beach
Chicago’s beaches not only offer a refreshing escape from the city’s heat during the summer, they are a pleasure to stroll on at any time of year. Stretching along the shores of Lake Michigan with more than 24 beaches to choose from, many are just a short walk or bus ride from the city centre. Favourites include North Avenue Beach which offers a host of water sports and cool beach bars, and the scenic Oak Beach, because of its proximity to Downtown.
15. Walk the Bloomingdale Trail
The Bloomingdale Trail, commonly known as ‘The 606’, (due to the numbers in its locations zip codes), is an elevated greenway repurposed from a former railroad on Chicago’s northwest side. Similar to New York’s Highline, it is over 4km in length and connects Chicago’s hippest neighbourhoods. It accommodates walkers, joggers, cyclists, and skaters, with a chain of parks, vibrant sculptures and murals along the way.
Bar and Restaurant Recommendations in Chicago
My visit to Chicago was short and sweet so I don’t have as many restaurant recommendations as I usually have, but we did find some of the best rooftop bars in Chicago, a cool brunch spot, and the best pizza in Chicago.
16. Do Brunch at Beatnik
Beatnik on the River is the place to go for a glamorous Chicago brunch. Its bohemian decor, tropical cocktails and tapas-style menus make it one of the top Instagram locations in Chicago. There are tables inside, so make sure to pre-book a table on the terrace overlooking with river, where you will be greeted with a colourful display of flowers and stylish furniture.
The weekend brunch menu offers shareable Mezze boards and Shakshuka, as well as typical brunch favourites such as burritos, egg sandwiches and cheeseburgers.
17. Have a Deep Dish Pizza
You simply can’t visit Chicago without trying a Deep Dish Pizza – it is one of the top things to do in Chicago. Chicago invented the Deep Dish Pizza which is famous for its thick crust, cheese layers and chunky tomato sauce, all baked in a deep pie-like pan. Unlike traditional pizza, the cheese goes on the bottom, followed by toppings, and topped with a rich tomato sauce.
Lou Malnati’s Pizzeria is the place to try it – we stopped here on our Bikes Bites and Brews tour, and I can honestly say it was the tastiest pizza I ever had! Lou Malnati worked at Pizzeria Uno where the Deep Dish Pizza was originally created in the 1940’s, he later opened his own restaurant, and it is now a must eat in Chicago.
You can also book a Chicago Pizza Tour which takes you off the beaten path into Chicago’s neighbourhoods to savour the best pizza. I have linked one of the most top-rated small group tours below.
18. Take in Skyline Views from a Rooftop Bar
Enjoying a cocktail with an epic view of the skyline is one of the top things to do in Chicago, and luckily Chicago has plenty to choose from. We visited two favourites and I can certainly recommend them both.
London House Rooftop serves up tasty food and cocktails day or night. Catch amazing views of the skyline and river below from its large open air terrace. This is part of the London House Hotel, one of the best places to stay in Chicago, – you can this and more of my top hotel picks below.
Cindys is another super rooftop bar and restaurant that offers views over Millennium Park, the Bean and Lake Michigan. I didn’t dine here – I just enjoyed the cocktails! All dining tables were inside during my visit, so check when booking if you can dine outside.
19. Catch some live music
Experiencing live music in Chicago’s blues clubs or speakeasies is a must for anyone looking to tap into the city’s rich music scene. Known as the birthplace of electric blues, Chicago is home to legendary venues like Kingston Mines, as well as original speakeasies such as the Green Mill Cocktail Lounge – a favourite of Al Capone.
Larger venues such as the House of Blues offer nightly concerts and shows with a restaurant on site. I had the pleasure of seeing Darius Rucker here and it was an incredible show.
20. Get your Thrills at Six Flags Great America – Day Trip from Chicago
About an hours drive from Chicago is one of America’s top theme parks, Six Flags. With 16 roller coasters and a massive water park, there are rides here for all the family. Don’t miss the record‑breaking wooden coaster with a 180‑foot drop and the Wrath of Rakshasa, a 180‑foot dive coaster.
Where to Stay in Chicago
From luxury 5 star hotels in Chicago to top-rated budget hotels and family friendly options, I’ve listed the best hotels in Chicago to suit all tastes an budgets.
5 Star Chicago Hotels
For foodies looking for a modern luxury stay in Chicago, Nobu Hotel won’t disappoint. Considering its household name, it is reasonably priced for a five star hotel. As well as the signature Nobu restaurant, there is a more casual Japanese restaurant, as well as a rooftop bar hosting DJs and live music. A sauna, fitness centre, indoor swimming pool, and steam room are also available here.
The Viceroy is another 5 star hotel in Chicago that offers good value, especially when you consider its location and top-class amenities, including a seasonal outdoor pool, a rooftop bar and lounge with panoramic city views, and a state-of-the-art fitness centre. Oak Street Beach is just a 10-minute walk away so this is a great choice for a summer stay in Chicago. The Viceroy is also one of the best five star hotels for families in Chicago.
The Sofitel Magnificent Mile is located just 2 blocks from the Magnificent Mile, and is decorated in a stylish French style. The café offers locally-sourced French-inspired cuisine with a seasonal outdoor terrace and guests can enjoy city views from Le Bar’s floor-to-ceiling windows.
The Langham is one of the best hotels in Chicago and is located close to the Magnificent Mile in Downtown Chicago. All rooms have floor-to-ceiling windows offering views of the skyline, Chicago river or Lake Michigan, and there is a Spa and Wellness centre with indoor pool available.
Best 4 Star Chicago Hotels
L7 Chicago by Lotte is one of the best 4 star hotels in Chicago. It is rated Excellent on TripAdvisor, (4.9 out of 5 ) and offers great value too. Centrally located along the Chicago River in the famous Loop business district, and just 9 minutes’ walk from Millennium Park, its hard to beat this hotel for location and value.
All rooms include a yoga mat – so you can enjoy one of those free Yoga classes in Millennium Park if you happen to be visiting during the summer months! Free tea and coffee is also available in the lobby and family rooms are also available.
citizenM Hotels rarely disappoint and the citizenM Downtown lives up to their reputation. Centrally located in Downtown Chicago, just six minutes walk from Millennium Park, you can expect a modern hotel at a great price point.
If you are looking for a central hotel with a snazzy rooftop bar, then look no further than the London House Chicago. We dined here for lunch, and it is the place to be seen in Chicago! Located right on Michigan Avenue and just 10 minutes walk from Millennium Park, it also boasts a 24-hour fitness centre.
The Staypineapple at The Loop is an iconic hotel that was designed by a world renowned architect and features mosaic floors and marble ceilings. Centrally located in The Loop, this trendy hotel is a super choice for a unique stay in the city.
The Lowes Chicago Hotel is a super choice for anyone looking for a hotel with swimming pool in Chicago. Located in the heart of Downtown Chicago and top-rated on TripAdvisor, this centrally located hotel also boasts a rooftop lounge with views of the skyline, a modern restaurant and a fitness centre.
Best for Value Stays and Family Hotels in Chicago
The Riu Plaza offers great value for a central stay in Chicago, just 1km from Millennium Park, It is suitable for adults and families with deluxe family rooms sleeping up to five. There is a rooftop pool, fitness centre and bar on site and it receives great reviews from guests, many commenting on the superb price point.
Sable at Navy Pier Chicago is a top-rated hotel offering stunning waterfront views. There are plenty of dining options at the hotel, and plenty more at Navy Pier, which is just 8 minutes walk away. This is a great choice if visiting Chicago during the summer months, you can catch the fireworks every Wednesday and Saturday and enjoy fun fair rides and entertainment on Navy Pier.
The Royal Sonesta Chicago River North is a centrally located 4-star boutique hotel that has an indoor pool and sundeck. A free morning coffee and tea bar is provided and there are large suites that can sleep up to five. Its sister Hotel the The Royal Sonesta Chicago Downtown also offers great value and all rooms here have kitchenettes.
The Hilton Chicago Magnificent Mile Suites is a super choice for families looking for large family hotel rooms in Chicago. One and two-bedroom suites are available that sleep up to five and the rooftop pool adds to its appeal as one of the top hotels for families in Chicago.
The Homewood suites by Hilton Chicago-Downtown is a great value 3-Star all-suite hotel located in Downtown Chicago. It is a good choice for a family hotel in Chicago as all rooms have a kitchenette with stove and fridge, and some rooms sleep up to five. There is an indoor pool and fitness centre on site too.
The Arlo Hotel offers great value family rooms in a central location, just five minutes walk to Millennium Park. There is a restaurant and bar on site and is ideal for anyone looking for cheap hotels in Chicago that are a good standard for a friends or family stay.
How to get to Chicago
Chicago O Hare is one of the most connected airports in the US, and the fifth most connected airport in the world. You can fly daily from many international airports including Dublin to Chicago with Aer Lingus, which is the route I took. United Airlines also fly from Dublin and offer a year round service from Shannon airport.
The best way to get from the airport to the city centre is by train – it only costs $5 and the journey time is about 40 minutes. You can also buy an unlimited 7 day train ticket for $20 which will include your return journey to the airport, assuming you are staying less than 7 days. Taxis usually take about 1 hour but they can take longer at peak times.
I hope my top things to do in Chicago and will you plan a trip to this great city! While every effort is made to ensure accuracy, descriptions and costs are subject to change.
Some of the links in this post contain affiliate links, where I receive a small commission if a booking is made, but at no additional cost to you.
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