Things to do in Chicago

Activities, Tours, & Pizza

Chi-town, the Windy City, Second City - it doesn't matter what name it goes by, Chicago is a vibrant, diverse, and fun filled city to visit and one of the best places to travel in the US this year.

On the shores of Lake Michigan, Chicago has a rich history, beautiful parks to enjoy in the summer, and a waterfront that's unmatched in the great lakes region.

It's an ideal destination for big city excitement, culture & history, and family fun (and of course deep dish pizza). Chicago is great for an action packed long weekend, but we've enjoyed longer stays getting to know the city and it's different neighborhoods.

It can get pretty cold and windy (hence the nickname) in Chicago during the winter because of the proximity to the lake. Even though you can still enjoy the city in the colder months, Chicago comes alive in the late spring and through summer when festivals are happening, parks are filling up, and the city is bustling. In the summer you can take advantage of outdoor activities like kayaking the river downtown or taking a dip in Lake Michigan. Fall is just as beautiful and even though it might not have the New York City association with Christmas magic, we love Chicago around the holidays.

Getting to Chicago

Chicago is easily accessible from anywhere in the US. O'Hare is a United Airlines hub and has direct flights to all major US cities. There is a straight shot on the subway from O'Hare to downtown, but it takes at least 45 minutes. With moderate traffic it's under a half hour drive so we normally opt to take an Uber.

Midway, Chicago's smaller airport, serves the regional and discount carriers. Midway is slightly shorter both driving and on the subway (again a straight shot so no need to transfer). The airport is small so you don't need to show up as early when you depart - which is a prime opportunity to take the subway and save some money.

Although local commuters might disagree, we're always happy using Chicago's rapid transit system known as the "L". The partially elevated train system is extensive and has great coverage thanks to its hub & spoke design; all lines converge on a central loop that surrounds the downtown core.

Rideshare services are widely available, but we consistently find them to be a long wait. Traffic can get pretty slow downtown so either budget some extra time or jump on the L.

Top Things to do in Chicago

Second City

Unique to only two other cities (Toronto & LA), the Second City is an improvisational comedy troupe that has trained well known comedy and film legends like Mike Meyers, Steve Carrell, Tina Fey and Dan Akroyd. They offer a range of live shows that change every couple months. Always an incredible live performance, it's the perfect way to catch rising comedy stars up close.

We regularly attend the main stage production of Second City when we're in Chicago or Toronto, and it's always highly entertaining! We recommend buying your tickets in advance online and showing up early; seating is based on arrival time so getting there earlier gets you a spot closer to the stage.

Catch a Game

Chicago is home to legendary sports teams in all the major leagues - and the locals love their sports.

Chicago Cubs at Wrigley Field: One of the top things to do in Chicago is catch a game at the renowned Wrigley Field, the second oldest MLB stadium in the country. Wrigley Field is north of downtown, about 20 minutes on transit.

Chicago White Sox at Guaranteed Rate Field: Yes, Chicago has two MLB teams, so if you don't get your baseball fill at a Cubs game, you can check out the White Sox. The stadium is south of downtown, about 15 minutes on transit.

Bulls Basketball: Another iconic sports franchise, the United center is 20 minutes west of downton on transit and offers an electric atmosphere.

Blackhawks hockey: Also playing at the United center, Chicago is a huge hockey city and absolutely worth checking out a game.

Bears NFL: Playing in the beautiful Soldier Field along the waterfront, catching an NFL game in any city is an exciting experience and being one of the oldest NFL franchises with a rich rivalry and history makes the Bears a great one.

Take in a View

At one time the tallest building in the world, the iconic Willis Tower (Formerly Sears Tower) observation deck is 103 floors above the city. The glass floored ledge lets you stare straight down to the streets below.

The observation deck is open year round and you can confirm the opening hours on their website at It's great to visit any time of day but we particularly love it at sunset.

Take in a different view and check out the 360 Chicago Observation deck in the John Hancock building. Located just north of downtown and close to the lake, you can gaze south across the sprawling core. The 360 observation deck is 9 floors lower than Willis Tower, and instead of a glass bottomed floor, they have angled glass windows that let you stare down.

Similar opening hours are available here and can be confirmed online:

Kayak the River

You saw it from above, now see it from below! Probably the most unique way to see Chicago is by kayaking through the Chicago River. We suggest you start at the mouth where it gets fed from Lake Michigan and then head west under all the bridges until you hit the T at the South Branch of the Chicago River.

We loved seeing the iconic buildings from the water and our guide was incredibly informative about the history of the city. On a clear summer day, it was great exercise and one of our favorite Chicago experiences.

Book ahead online, and meet your operator along the Riverwalk.

Hit the Lake

Take advantage of the incredible waterfront Chicago offers. There's plenty to do just off downtown, but if you have time to head north or south you could literally spend your entire long weekend doing activities along the shore and not run out. Some of our favorites include:

Head to the Beach: Beaches are scattered along the water. Small, urban ones like Ohio Street Beach leave you feeling like you're still in the city, so we recommend heading north to North Ave Beach or Montrose Beach. Oak Street Beach offers one of the best shots of the skyline meeting the lake.

Stand up Paddle Boards: Budget friendly, great exercise, and the ideal refresher on a hot Midwest summer day. You can rent boards all along the waterfront for as little as $30 an hour. Most of the beaches have plenty of suppliers.

Boat Rides: Take advantage of beautiful Lake Michigan the way it's meant to be enjoyed; on a boat! There are sailing lessons, fishing trips, craft beer cruises, and pontoon rentals so you can go at your own pace.


A diverse array of neighborhoods make up Chicago. The city is proudly a large mix of unique neighborhoods so have some fun exploring and learning about the different areas. It will give you a great perspective on the history of Chicago and you're bound to find new and exciting things to do. There is still the reputation of some dangerous neighborhoods in Chicago. However, you have to go pretty far south or west to get into the pockets with the reputed high crime rates, so use your best big city judgement, and if in doubt, ask a local.

The Loop, Near North, & Navy Pier
The downtown core, or The Loop, is the most well recognized and typically where visitors spend most of their time, along with Near North & Navy Pier. It is an amazing part of the city to explore, and you could easily spend your entire visit just doing activities here. Some of the best parks, museums, and tourist attractions are here, so don't be surprised when it starts to look familiar after spending a lot of time.

Lincoln Park & Old Town
We love it for the massive Lincoln Park that stretches along the shore - and the young population means great bars and restaurants scattered throughout.

Named after its star attraction, Wrigley Field, Wrigleyville is a great stop for nightlife. Particularly when the Cubs are playing this neighborhood comes alive and a large concentration of bars and restaurants fill up. Even better on home game nights!

Museums in Chicago

A great museum city, here our favorites:

Field museum: Our personal favorite, this huge museum is dedicated to science and natural history. Bonus, they have the largest T-Rex skeleton in the world, along with a cast of a titanosaur which is larger than a blue whale!

Museum of Science and Industry: Not just for kids, the Museum of Science and Industry has a German submarine and a 1910-era "Main Street".

Art Institute of Chicago: Probably the most well-known and impressive museum in the city, this is a must for any art lover. Located in beautiful Grant Park, the iconic building is the first site to marvel at during your time here.

Navy Pier

Navy Pier can get a little touristy, especially in the summer, but it's worth spending an afternoon. To start, you get amazing views of Lake Michigan, and the opportunity to admire the downtown from a different angle. In fact, it's worth going to the end just to see the skyline in all its glory.

There's restaurants, rides & attractions including a ferris wheel, a theatre, and shops along the entire pier. They also have a great kids museum (more about Chicago for Kids). We love going when there are events on and they regularly have live music. Check out the event calendar to time your visit:

If you only make it to navy pier for one reason, go on Wednesday or Saturday evening during the summer for the fireworks show!


Chicago is consistently considered a top parks city in the US. The easily accessible Lakefront trail is 18 miles long, starting at the top of Lincoln Park in the north end running right to downtown. Walk, run, blade, or bike along the water and stop in at some of the beautiful parks that make up Chicago.

Lincoln Park: 1200 acres and the start of the Lakefront Trail, you could spend a day here and not run out of free activities. The zoo, conservatory, and cultural center are all free.

Grant Park: The massive park covers part of The Loop and heads along the waterfront south. Made up of many other smaller parks, it includes Buckingham Fountain, the Art Institute, and Museum Campus, which features the aquarium, Soldier Field, the Field Museum and Planetarium.

Millennium Park: In the same area as Grant Park, you'll likely stop here at a minimum to see the famous Bean Statue (AKA Cloud Gate). An outdoor theatre, restaurants, and nearby ice skating rink & playground (Technically in Maggie Daly Park) make it a beautiful part of the city which is easily accessed from The Loop.


We didn't add it to the list because you already know to get some deep dish pizza in Chicago. There's a couple well known ones that are all great: Giordano's, Lou Malnati's Pizzeria, and Uno.

New York style or Chicago deep dish pizza? The debate rages on. A lot of travelers compare Chicago to New York City, and say it will never be NYC. But Chicago is uniquely its own and doesn't NEED to be NYC. It has a unique energy, vibrant art & culture scene, and it's own history that makes it a place we keep going back to. Don't go in with expectations of a lesser NYC, go in expecting to discover something new and amazing, and you'll inevitably leave wanting to return.

- Jason Kraemer

Jason Kraemer is the co-founder of Flashpacker Co, a lifestyle brand aimed at helping the growing number of global flashpackers get the most out of their adventures - experiencing more by sacrificing less. Follow Flashpacker on Instagram @FlashpackerCo and their website:

If you have a limited amount of time for your journey, see our advice about how much time to spend here: Should I spend 1, 2, or 3 days in Chicago?, Should I spend 3, 4, or 5 days in Chicago?, Should I spend 1 or 2 weeks in Chicago? and Is Chicago Worth Visiting?

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