What’s great about Chicago is that there is something to do any time and every day of the week -- even on a Wednesday. Weekdays can get mundane, so spice things up midweek! With all of the amazing restaurants, museums, entertainment, and parks, there are plenty of fun things to do on a Wednesday in Chicago.
It’s also a great day to beat the crowds at some of the city’s most popular attractions. We’ve rounded up a list of the best things to do in Chicago, so you can make your next hump day one to remember.
Things To Do In Chicago On a Wednesday
Jazzin’ at The Shedd
Every Wednesday evening from August to October, The Shedd Aquarium hosts a cocktail party, called Jazzin’ at the Shedd. Enjoy great music, a full bar, access to exhibits in the aquarium and the stunning Chicago skyline. If you go before Labor Day, you can also see the Wednesday night fireworks over Lake Michigan. The Shedd Aquarium (1200 S Lake Shore Dr, Chicago, IL 60605) houses more than 32,000 animals and has some of the best exhibits in the world. Enjoy Jazzin’ at the Shedd on Wednesdays for $25.
Enjoy Live Music at a Speakeasy
Celebrate hump day with a toast! Chicago is known for its speakeasy bars and music, and on Wednesdays you can enjoy both of those things. The Bassment in River North and Bordel in Wicker Park have live music every Wednesday in speakeasy-inspired settings. Check out my list of the best speakeasies in Chicago and how to get inside!
Try a new BYOB Restaurant
When you want to eat out midweek without spending a ton of money, check out a BYOB restaurant. One of my favorite BYOB spots is Irazu in Bucktown (1865 N Milwaukee Ave, Chicago, IL 60647). It’s a Costa Rican restaurant where your money goes far, the food is fantastic, and the portions are large. There are lots of vegetarian options on the menu too. I always start with ordering vegetarian Chifrijo, which is fried pork (optional) layered with black beans, rice, pico de gallo, avocado and Lizano sauce. Grab some friends, a bottle of wine, and come here next Wednesday!
Go to the Theater
Chicago has a vibrant theater scene and tickets are often cheaper on a Wednesday. Windy City Playhouse in Irving Park (3014 W Irving Park Rd, Chicago, IL 60618) is home to exceptional shows. I saw Southern Gothic there, and it was such a unique experience (check out my review of the play!). There are only 30 people in the audience and you are actually on set, inside a house, during a 1960’s cocktail party watching the drama unfold up close.
Visit The Art Institute
The Art Institute of Chicago has some of the most iconic artwork in the world such as Grant Wood’s American Gothic, Pablo Picasso’s The Old Guitarist and many more. Right now, it’s rated the #1 thing to do in Chicago on Trip Advisor, so go on a Wednesday to beat the weekend crowds. By the way, read my review of another, unconventional way to see the Art Institute of Chicago.
Get Drinks in the Sky
During the summer, take advantage of the warm weather with cocktails at a rooftop bar. Some of my favorites are the J. Parker, London House, and Aba. Rooftop spots are super crowded on the weekends, so come on a Wednesday at 5pm to snag a good seat.
Catch a Concert and Dinner at Thalia Hall
Make Wednesday count with a show at Thalia Hall (1807 S Allport St, Chicago, IL 60608) a historic landmark in Chicago’s Pilsen neighborhood. Thalia hall has three levels -- each with a great vibe. On the main floor you’ll find a restaurant that pairs food with beer. On Wednesdays, they offer half-priced bottles of beer and wine with a food purchase (the deal is active as of this publication date). The lower level houses a punch-focused cocktail bar serving fondue. Upstairs you’ll find a rad music venue and event space.
Watch Wednesday Fireworks at Navy Pier
Make Wednesday night, date night at Navy Pier. After sundown on Wednesday nights in the summer, you can catch a spectacular fireworks show at Navy Pier. The Wednesday night fireworks shows run from Memorial Day to Labor Day every year.
Go for a Ride at Navy Pier
Navy Pier received a $300 million renovation over the last few years, and it makes a fun date night year round. My husband and I visited Navy Pier during a Chicago staycation and we had the best time! Take my advice and go on the swings! Seriously, it’s such a fun way to spend $9. We were laughing like kids while soaking in the city’s skyline lit up at night. The new ferris wheel offers stunning views of the city as well. If you splurge on the Centennial Wheel VIP experience you’ll also enjoy views from the glass-bottom gondola. You can watch my video on the VIP ferris wheel experience to decide for yourself if you want the upgraded tickets.
Lincoln Park Zoo After Hours
During the summer, Lincoln Park Zoo hosts special events in the evenings. For example, you can go to Café Brauer (2021 N Stockton Dr, Chicago, IL 60614) located at the zoo’s beautiful Nature Boardwalk for live music on the patio from 5:30-7:30 in the summer. You can also try a Fitness at the Zoo class during the summer through the end of September.
See the Animals at Lincoln Park Zoo
If you have the day off or friends in town, Lincoln Park Zoo (2001 N Clark St, Chicago, IL 60614) is a great place to visit on a Wednesday. It’s located near North Avenue Beach and Lincoln Park and it’s free, so you can walk through the beautiful grounds and stay for as long or as little as you like. The zoo closes at 5:00 pm on Wednesdays.
Try a New Restaurant
It’s not hard to find quality food and drink in Chicago, and there is always new additions to Chicago’s famous restaurant scene. Make a point to try something new next Wednesday, like Etta in Bucktown. The restaurant comes from the chef and owners behind the posh steakhouse, Maple & Ash. You can enjoy wood-fire pizzas, pastas, and fresh salads.
Enjoy the Lakefront
When the weather is warm in Chicago, we have to take advantage of it! Chicago’s lakefront trail is 26 miles long, and is active with runners, yogis, and people just relaxing. Oak Street Beach is located in the Gold Coast neighborhood of Chicago, where you are nestled between Lake Michigan and the iconic skyline. North Avenue Beach is the most sceney beach and a popular spot to play volleyball or chill out with friends. There are tons of fun things to do in Chicago on a Wednesday along the lakefront.
Explore the Museum of Science and Industry
If you have the day off, head to The Museum of Science and Industry (5700 S Lake Shore Dr, Chicago, IL 60637) to experience one of the largest science museums in the word! Control a 40-ft tornado, tour a WWII submarine, and enter a mirror maze at the 400,000 square foot museum. The special exhibit called The Science Behind Pixar is on my list (running through January 6,2019). The Museum of Science and Industry is located in Hyde Park near the University of Chicago.
In the winter, you can go ice skating near The Bean, and during the summer you can listen to live music at the Jay Pritzker Pavilion (201 E Randolph St, Chicago, IL 60601). The summer music series takes place on Wednesday evenings. You can buy some food and wine from Mariano’s across the street to have a picnic in the park during the concert. Or keep it simple with pizza from Lou Malnati’s which is also across from the Jay Pritzker Pavilion.
Take a Walk in the Park
Escape the hustle and bustle of the city buzz, without ever leaving Chicago. Head to one of Chicago’s 570+ parks to wind down from the work day. Maggie Daley Park, Grant Park, and Lincoln Park are some of the most popular parks in the city, but there are hundreds throughout the city. Afterall, Chicago’s motto is “urbs in horto,” which means “city in a garden.”
Make the most of your next hump day with one of these things to do in Chicago on a Wednesday! You might also check out Five Creative Second Date Ideas.
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Thank you to Natalia Quino, Karina Montelongo, and Madeline Doherty for contributing to this video and article.
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