Ahhh Chicago. The city most near and dear to my heart, and my home away from home. I grew up just outside of Chicago, and I can honestly say that the city remains one of my very favorite places in the world. There are so many wonderful things to do in Chicago, and it is the perfect destination for any traveler in search of a getaway weekend.
Traveling to Chicago is wonderful at any point in the year, as Chicago offers an endless number of activities that adjust with the changing seasons. Summers bring boating, beaches, and rooftops, while Winter brings mugs of hot chocolate and ice skating. Autumn and Spring are the most beautiful times to stroll through the gorgeous parks.
Below are my top recommendations for activities to explore in Chicago!
17 things to do in Chicago
1. Visit the Museum of Science and Industry
The best museum in the entirety of Chicago has to be the Museum of Science and Industry. The museum is located in Hyde Park (off the south shore line), and is housed in a building that was constructed for the 1893 World’s Fair.
Many of the exhibits are interactive, making it an excellent place for both children and adults to explore. Some of the best standing exhibits include Old Town Main Street, the baby chick hatchery, and the science storms. There is also an incredibly intricate fairy tale dollhouse, a model train exhibit that displays all shipping routes from San Francisco to New York City, and a Rube Goldberg machine that spans nearly an entire atrium.
For an additional cost, you can purchase tickets to enter the Coal Mine or U-505 German Submarine. Tickets for these exhibits book out months in advance – so I recommend blocking them out well ahead of time.
Cost: A single day ticket to the Museum of Science and Industry costs $22 USD for adults, and $13 USD for children under 13. Additional tickets to the coal mine cost $12 for adults and $9 for children. The U-505 German Submarine tour (as well as additional tickets to touring, part-time exhibits) costs $18 USD for adults, and $14 USD for children under 13.
2. See a show at the Chicago Symphony Orchestra
The Chicago Symphony Orchestra is located just across the street from Millennium Park. The CSO was founded in 1891, and runs over 150 unique concerts per year.
The theater itself is gorgeous, and certainly worth a stop for any fans of music. My personal favorite concerts are part of the “CSO at the Movies” series. With this series, the orchestra plays the entire film score of a Hollywood blockbuster, while the movie plays from start to finish on a giant projector. I’ve attended Harry Potter and the Sorcerer’s Stone, Star Wars: Return of the Jedi, Home Alone, Pixar in Concert, and Lord of the Rings: The Fellowship of the Ring. This experience has knocked it out of the park every single time. I cannot recommend it enough!
Tickets cost anywhere from $50-200 USD depending on seat selection and the concert that you want to attend. Check out the CSO’s official website for dates, ticket prices, and upcoming concerts.
3. Venture to the top of the Willis (Sears) Tower Skydeck
Have you ever wondered what it would be like to stand in a suspended glass box hundreds of feet in the air? Look no further than the Willis (Sears) Tower Skydeck. Yes. I will continue to write ‘Sears Tower’. That is what it will always be to me… even though the technical name is Willis Tower now.
The skydeck is open all year round, with slightly shorter hours in the winter. Because the Willis Tower is one of the tallest buildings in Chicago, you will get some of the best views of the city from this vantage point. It is certainly not for the faint of heart!
Cost: The skydeck pass on the weekends costs roughly $42.50 USD for adults, and $33.50 USD for children under the age of 12. However, ticket prices may fluctuate depending on the time of week and time of day. Check the Skydeck’s ticketing website for the most up-to-date information on prices and availability.
4. Attend a Cubs game at Wrigley Field
You did not actually go to Chicago, if you did not attend a baseball game at the historic Wrigley Field – home of the Chicago Cubs. Attending a Cubs game in the summer is one of the best things to do in Chicago. There is such an energy to Wrigleyville that is almost palpable.
The field was built in 1914, and still has the original, manual scoreboard in far center field. You’ll have the opportunity to see the famous ivy covered walls and, if the Cubs win, you’ll watch them “Fly the W” around the outfield while the entire stadium sings.
Grab some peanuts and beer and enjoy! The bleacher seats are a rowdy and fun time, if you are looking for something a bit more budget-friendly. And if you happen to be in town during the cross-town rival (Chicago Cubs vs. Chicago White Sox) then you’re in luck! That game is a must-see.
Cubs tickets cost anywhere from $16 – $80 USD depending on the type of seat you are purchasing and the opponent of the game. Obviously, the cross-town rival (or other rivalry games, like the Cardinals) are going to be a bit more expensive. But those are always the most fun games. Check out the MLB official website or Stubhub to purchase tickets.
5. Take an architectural boat or walking tour around the city
The Chicago Architecture Center offers free walking tours that showcase some of the most magnificent buildings in the heart of downtown Chicago. You can learn a bit about the city’s history – including how the Chicago Water Tower building is one of the last remaining structures from before the Chicago Fire in 1871.
The architectural boat tour is a uniquely fun experience. You will float down the Chicago River and learn about all of the buildings that line the banks. This tour was rated the number 1 boat tour in North America in 2021. It is definitely worth the hype!
Cost: Walking tours of the city typically cost in the $30 USD ballpark, whereas an architectural boat tour costs closer to $50 – $60 USD depending on the type of tour booked. The Chicago Architecture Center offers a slew of tours on their website. I recommend checking out their official website to find a tour that best fits your requirements.
6. Do some vintage shopping in Wicker Park
Wicker Park is perhaps one of the most “hipster” neighborhoods in Chicago. Full of art, patios, and vintage shopping, it is a great neighborhood to spend a day in. Wicker Park is most easily accessible from the ‘Damen’ stop on the Blue Line.
Some of my favorite stops in the are include Myopic Book, Vintage Underground, and Store B Vintage. If you walk along Milwaukee Avenue, you are guaranteed to find some unique items to add to your fashion collection.
For more information, check out my ‘Chicago Neighborhood Guide’ here.
7. Stop by the Peggy Notebaert Nature Museum
The Peggy Notebaert Nature Museum is a very unique stop on this Chicago tour. Located just north of the Lincoln Park zoo, this museum pays homage to the diversity of wildlife and flora that exist in Illinois. The museum also has a slew of outdoor nature walkways that allow you to get a breath of fresh air as you explore.
The best component of the Peggy Notebaert is the Judy Istock Butterfly Sanctuary. This is a massive room filled with monarch butterflies and flowers. You could easily spend a few hours here just watching them fly about and, if you’re lucky, maybe a few will land on you for good luck!
Cost: The Peggy Notebaert costs $15 USD for Illinois residents and $17 USD for out of state residents. Children cost $8 USD for residents, or $10 USD for out of state visitors. Check out their website to purchase tickets.
8. Watch the Rocky Horror Picture Show at the Music Box Theater
The Music Box Theater is a small, iconic cinema located walking distance from Wrigley Field. The theater was built in 1929, and has retained much fo the same interior and charm that it had when it was first constructed.
The Music Box operates as a traditional movie theater, offering the latest and greatest from Hollywood. However, one of the best reasons to attend the Music Box is to see a midnight production of cult-classic The Rocky Horror Picture Show. Rocky Horror plays roughly once per month at The Music Box, and is always accompanied by a shadowcast, who perform live on stage while the movie plays in the background. Everyone attends the theater in costume, and screams at the screen continuously throughout the film. It is absolutely worth a fun evening out!
Cost: Tickets to The Rocky Horror Picture Show at the Music Box Theater cost $12 USD. I recommend booking in advance, as they sell quickly!
9. Attend a concert at the Chicago Theater
The Chicago Theater is one of the most iconic landmarks in Chicago. Located in the heart of the Chicago theater district on State and Lake, the theater’s marquee lights up the path from blocks away. The theater was built in 1921, and offers a variety of musicals, stand-up comedy shows, concerts, and lectures. The interior of the theater is absolutely stunning. If you have the opportunity to attend a show here, I highly recommend doing so!
Cost: Ticket prices will depend greatly on the performance and seating location. You can find information about upcoming shows and ticket prices on the official Chicago Theater website.
10. See a performance at the Chicago Shakespeare Theater
See a performance at the Chicago Shakespeare Theater
Located at Navy Pier, the Chicago Shakespeare Theater is one of the staple landmarks in the city. I have vivid memories of attending many a school field trip here (and one extremely vivid memory of one actor accidentally projecting a glob of spit directly onto his co-star’s face).
The theater puts on upwards of 20+ different productions per year, which amounts to well over 600 individual performances. The Shakespeare Theater also has a knack for putting modern twists onto the Bard with the Beard’s original text – keeping the classic stories engaging for younger audiences. The Youth Shakespeare wing of the theater is particularly impressive as well. SO much talent. If you are a fan of Shakespeare, this theater is certainly worth a stop.
Cost: Ticket prices will depend greatly on the performance and seating location. You can find information about upcoming shows and ticket prices on the official Chicago Shakespeare Theater’s website.
11. Stroll through the Art Institute of Chicago
I know I said the Museum of Science and Industry was my favorite museum in Chicago – but the Art Institute is a close contender. The Art Institute houses a collection of art spanning centuries across the entire world. Here you can see famous pieces by Salvador Dali, Vincent van Gough, Georges Seurat, and many, many more.
Some of the most well known pieces in the Art Institute include: Self Portrait by Vincent van Gough, America Windows by Marc Chagall, American Gothic by Grant Wood, A Sunday on La Grande Jatte by Georges Seurat, and The Old Guitarist by Pablo Picasso. It is well worth it to spend the afternoon wandering the magnificently lined hallways.
Cost: Tickets to the Art Institute cost $25 USD for non-Chicago residents, and $14 USD for Chicago residents. Children under the age of 13 enter for free. The museum is open everyday except Tuesdays and Wednesdays. Check out the Art Institute official website to purchase tickets.
12. Ice skate in Millennium Park
One of the best things to do in Chicago in the winter is ice skating. There are many opportunities to bring out the blades! But the most popular ice skating spots in the city are in Millennium Park. The McCormick Tribune ice rink and the Maggie Daley Park rink (the Ribbon) are a favorite spot for tourists looking to skate in the snow.
The rinks are open from late-November to early-March from 8am – 9pm (weather permitting). The rinks are free to use, but do require a reservation in advance. Skate rentals cost $13 USD during the week, and $15 USD on weekends.
13. Marvel at the Zoo Lights
For the holiday season, Lincoln Park Zoo is decorated to the nines with twinkling fairy lights. You could easily spend a few hours strolling through the light exhibitions while sipping mulled wine or hot chocolate.
Zoo Lights typically opens in mid-November, and runs through early January. It is the perfect wintery activity to help get you in the holiday spirit.
General admission tickets for Zoo Lights cost $5 USD – which is super reasonable. However, admission is free on Mondays. Just be aware that parking does cost a considerable fee – so I recommend taking public transportation if you can!
14. Watch the Joffrey Ballet perform the Nutcracker
The Joffrey Ballet, founded in 1956, is the most well-renowned ballet company in Chicago. The company performs a variety of productions year-round in the Lyric Opera House. However, my personal favorite is their annual production of The Nutcracker.
The Joffrey Ballet’s performance of The Nutcracker is one of the best ways to get into the holiday spirit. Pyotr Ilyich Tchaikovsky’s iconic score, accompanied by some of the best dancing, costuming, and production design, is truly unmatched. If you happen to be in Chicago during November and December, I highly recommend adding The Nutcracker to your bucket list. If you are traveling during a different time of year, seeing a Joffrey Ballet production is still a great way to spend an evening.
Cost: Ticket prices will depend greatly on the performance and seating location. You can find information about upcoming shows and ticket prices on the official Joffrey Ballet website.
15. Shop on the Magnificent Mile
The Magnificent Mile, located on Chicago’s Michigan Avenue, is one of the most well known sections of the city. Michigan Avenue is basically Chicago’s Fifth Avenue – it is home to all of the luxury clothing brands like Burberry, Gucci, and Louis Vuitton. It is also home to the Water Tower building (one of the last remaining structures from the Chicago Fire), and the subsequently named Water Tower Mall, which is home to the American Girl Doll store and the Lego Store.
If you are looking to drop some serious cash on a shopping spree, then this is the place to do it. In my personal opinion, there are better hidden gems in the city. But to each their own!
16. Go boating on Lake Michigan
Chicago is fortunate enough to sit along the coastline of the unmatched Lake Michigan. One of the best things to do in Chicago during the long and hot summer months is to charter a boat to cruise out into the water.
Most of these boat rentals will offer opportunities for you to take a dip into the water and float around for a while. Others offer more of a “boozy” variety. Lay back, sip some wine, and enjoy the summer sun.
Listen – the Midwest is COLD AS HECK in the winter. As a result – we take our boating season seriously. There are seemingly endless
If you are looking for a cheaper or shorter alternative, many beaches offer hourly stand-up paddleboard or kayak rentals.
Cost: Boat rental costs vary greatly depending on the type of boat you are looking to charter, and the length of your tour. To help keep costs down, I highly recommend embarking with a larger group. The larger the group, the lower the cost per person. Check out Boatsetter.com to search through the various boat rentals offered in Chicago at any given time.
17. See a show at the Second City
Rounding out the list is one of my personal favorite activities in Chicago – The Second City. The Second City is a well-known, historic improvisational theater company based out of Chicago. The theater is located in Old Town, and offers a variety of hilarious live performances almost every night of the week.
In addition to being a fully-operated theater, The Second City is also known for its award winning training center. What makes the theater so remarkable is the seemingly endless list of famous alumni who went on to make waves in the comedy scene. Some notable alumni include: Tina Fey, Amy Poehler, Bill Murray, Stephen Colbert, Amy Sedaris, John Belushi, Jason Sudekis, and Steve Carell. And that just scratches the surface!
If you are heading to Chicago, attending a Second City performance is a MUST. The theater has some of the best vibes – and the shows are nearly always hilarious. If you are interested in performing comedy yourself, I recommend looking into a drop-in improv class at the Second City Training Center. Classes are typically two hours, and are a ton of fun.
Cost: Ticket prices will depend greatly on the performance and seating location. You can find information about upcoming shows and ticket prices on the official Second City website.
That’s all, folks!
Hopefully this guide helps kickstart your Chicago itinerary! Even though I’m a bit biased from growing up in the area, Chicago remains one of my favorite cities in the world.
Check out my list of free things to do in Chicago and my Chicago neighborhood guide for more inspiration!
Have you been to Chicago? Drop a comment with some of your favorite activities below.
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