For those of you who don’t know, this is my birthplace, the Windy City. Everybody I meet while traveling gets the same quote from me – “come to Chicago is the summer between June and the first 2 weeks of September. It’s one of the best cities in the world for 3 1/2 months”.
Summertime Chicago has a lot to offer because the weather isn’t a deterrent during this season. Moreover, the locals are happier and more enthusiastic, translating to an overall better energy in the city. It’s nice to be somewhere where the people that live there are in a better mood.
There are a million things to do here, but I’ve consolidated them to 11, and I’ll try not to list all the most obvious stuff that you might see in other blogs or articles. If you don’t find certain major activities, I left them out on purpose.
Without further adieu, let’s go!
1. See a Chicago Blackhawks Game + Jordan Statue
This is an extremely underrated activity for any traveler, and is especially exhilarating for a hockey fan! When the team is having a good season, even better. For those who don’t know, the Blackhawks are our professional hockey franchise (NHL). If you’ve never been to a hockey game at this level, check it out because it’s a memorable experience when seen live and in person.
Chicago has very loyal sports fans in general and a rich history in hockey, American football, and basketball, so you will witness a lot of passionate attendees. One of the most unique aspects of the event here is the singing of the United States national anthem, which it’s uniquely electric.
Try to attend a game against the Detroit Red Wings or the St Louis Blues, the Hawks’ biggest rivals. If not, hopefully catch a good matchup against another high quality team. The United Center, the stadium where the team plays, is also home to the Chicago Bulls and the famous Michael Jordan statue.
2. Visit a Street Fest
During the summer months, Chicago is home to a ton of different street festivals, ranging from cultural, artesanal, food, music, literature, etc. Typically 2-4 blocks of a street are closed off just like any other street market with vendors and stages. The fests take place on weekends, starting Friday evenings and ending on Sunday nights.
You can find them on local event websites (currently Bucket Listers and The Haute Seeker), Choose Chicago, or Facebook groups. There’s typically something happening every weekend during the Summer. Don’t miss it!
Not all fest are equal, so do some research before you attend one. You don’t want to be disappointed if something turns out to not be the vibe you want. Some are crowded, some are chill. In the end there’s something for everyone, including the major music festivals found here https://www.choosechicago.com/articles/chicago-music/top-summer-music-festivals-in-chicago/
3. Art Institute & Museum of Science and Industry
These are the best museums in city, and I highly recommend you pay them a visit. The Museum of Science and Industry in the largest science museum in the Americas, house in a historic building dating back to the 1893 World’s Fair. It has an educational focus with several engaging and interactive exhibits spanning science, technology, engineering, and industry, while being home to thousands of artifacts.
The Art Institute is continuously rated as one of the best museums in the world. It showcases iconic masterpieces in modern and contemporary art, ancient and Asian art, and American and European paintings. There are of 300,000 works of art across all mediums in the museum’s permanent collection. Plan to spend a lot of time here if you’re a fan of art.
The Art Institute is conveniently located just a few blocks from The Bean (Cloud Gate), the notorious sculpture and famous landmark.
4. Grab a Coffee and Walk/Bike/Roller Blade the 606
The 606, or Bloomingdale Trail, is a about a 4km-long elevated linear park (basically a bridge), about 7 meters above the street level, running east–west along Bloomingdale Avenue between Damen Avenue and Lawndale Avenue on the northwest side of Chicago. It’s open from 6am-11pm (sometimes there are night activities).
I suggest grabbing a coffee or smoothie from a nearby shop in the Wicker Park neighborhood, then entering the 606 from the entrance at the intersection of Milwaukee Avenue and Leavitt Street. Relax and enjoy the beautiful views.
5. Standup Comedy, Improv, Theatre, Live Music
Chicago has a historic comedy scene and a rich history of live shows in general. You should enjoy it while you’re here. Some of the most notable venues for comedy are Zanies, The IO theatre (live improv), and The Laugh Factory. The Second City is also famous but I don’t personally like it. I particularly enjoy Zanies for the intimate setting. Enjoy the talented performers and have a few laughs.
For plays and live acting, consider the prestigious Goodman Theatre, our oldest non-for profit theatre, founded in 1922. It’s an internationally recognized venue with 2 performance spaces, known for its variety of productions, including classic dramas, musicals, and world-premiere productions. It is community focused, and even offers pre/post show discussions.
Next we have one of the most recognizable landmarks in the city, The Chicago Theatre. The iconic venue showcases concerts, comedy shows, family events, theatrical performances, and even podcast shows. Even if you decide not to see a show, book a tour of the theatre to view it’s magnificent interior and get a behind the scenes look at it’s storied past. Just make sure you find a good tour operator.
For live music I suggest going to Subterranean, The Green Mill, The Empty Bottle, and Kingston Mines. Each place caters to a different crowd with different kinds of music. Check them out and see which one suits you. All of them are local joints, but by far the most touristic is Kingston Mines.
6. Garfield Park Conservatory
The Garfield Park Conservatory functions as a “landscape art under glass”, housing thousands of plant species within eight indoor gardens and 10 acres of outdoor gardens. Each indoor space simulates a distinct ecosystem.
- The Fern Room recreates a prehistoric, swampy landscape with ferns and a lagoon.
- The Palm House features a tropical environment with over 70 palm trees.
- The Desert House contains a collection of cacti and succulents.
- The Aroid House displays a variety of aroid plants, some of which are popular houseplants.
- The Show House hosts rotating seasonal floral exhibits.
The conservatory also features special exhibits and a Children’s Garden designed for educational purposes. It’s a pleasant getaway and takes you to another area of this large metropolitan city. I would recommend taking an Uber here.
7. Jim’s Original & Mario’s Italian Lemonade
Out of all the Chicago classic street foods, the Polish is my favorite. Jim’s Original is the godfather. They prepare the perfect blend of sausage, mustard, sport peppers, and grilled onions. Located near the University of Illinois at Chicago (UIC), it’s conveniently situated around a bunch of other bars and restaurant just a block or 2 away on halsted street.
About a 10-15 walk from here at 1068 W Taylor St you will find Mario’s Italian Lemonade. After your polish sausage walk over to Little Italy and get yourself a deliciously refreshing Italian Ice/Lemonade. Usually open from May to mid-September, Mario’s Lemonade is a staple in the neighborhood. In order to go from Jim’s to Mario’s, you can conveniently walk through the UIC university campus.
8. Get a bike, Ride Around the City & Along Lake Michigan
Chicago is a GREAT city to bike. After I finish the Lake Michigan part, I’ll give you some bike friendly streets and areas to explore via bicycle if you want to explore outside of the downtown area, which you definitely should.
Riding along Lake Michigan will make you want to live here. On one side you have a immense lake and beaches, and on the other side Lake Shore Drive and some huge apartment buildings. Generally speaking you’d want to take the Lakefront Trail. Some notable locations that you should consider during your ride are Montrose Beach, Belmont Harbor, Chicago Yacht Club, Dusable Harbor, and Diversey Harbor areas. There’s a lot to explore.
Moving on to some more local routes:
- Milwaukee Ave going northwest and southeast between Halsted St and Kimball Ave. This is about a 7.5 km stretch that passes over the Kennedy expressway, and through the Wicker Park and Logan Square neighborhoods. It’s a very bike friendly route. Wicker Park and Logan Square have a lot going on themselves, full of shops and restaurants. Feel free to do your own research or explore the areas.
- Humboldt Park is a enormous park that you can ride through on your bike. The 2 major streets leading to the park, North Ave and Division St, are both equipped with safe bike lanes. Get some Puerto Rican food on Division street while you’re at it.
- Lincoln Ave going northwest or southeast in between Fullerton Ave (Lincoln Park) and Lawrence Ave (Lincoln Square). You will traverse different residential neighborhoods and get a authentic Chicago commuter experience.
- Take Clark St going north or south in between Fullerton Ave and Irving Park Ave which passes through Wrigleyville, or take Broadway Ave in between Diversey Ave (Lakeview) and Argyle St (Vietown or Little Asia).
Each of these routes will provide a different experience. See which one may be most appealing to you by checking them out google maps.
9. Architecture Boat Tour & More Architecture Tours
Ideally taken on a nice sunny day, this tour navigates the Chicago River downtown. Chicago is renowned for having a stunning skyline, which many say is the best in the United States. During the tour, you will learn about important history including the Chicago fire and the rebuilding that happened in the aftermath, the various architectural styles and buildings were constructed along the river, several landmarks, famous architects, and the city’s innovation in constructing the modern skyscraper.
The clear reflections off the glass windows of many buildings is a wonderful accent to the tour, which is why I suggest going on a sunny day. Walking around the streets and looking up at the gorgeous architecture is one thing, but witnessing it from the River takes you to a different dimension.
MORE ARCHITECTURE (QUICK RUNDOWN)
- Hyde Park – a deeply cultured neighborhood home to the beautiful University of Chicago, the Frederick C Robie House designed by legendary architect Frank Lloyd Wright, Osaka Garden, and a selection of gorgeous victorian houses
- Loop and Financial district interior architecture tour. You will miss out on a lot by not going INSIDE these fantastically desgined buildings. I’ve left a link to a tour here. If it expired by the time you read this, you can easily look for another one. I highly recommend this. https://www.tripadvisor.com/AttractionProductReview-g35805-d11474882-Original_Chicago_Architecture_Interiors_Tour_Dazzling_Interiors-Chicago_Illinois.html
- Frank Lloyd Wright Home & Studio Tour. Check out the home of the highly influential architect and designer known for his organic concepts. A must see for anyone interested in design concept. A jewel of a place.
10. Order the Gourmet Mix from Garrett Popcorn Shops
Home of my favorite popcorn. I’m traditionally very strict with my diet so I don’t eat anything like this anymore, but I can’t deny it is delicious and ADDICTIVE. This establishment was founded by Gladys Otto Garrett in 1949 and still stands today.
Get a taste of Chicago history and be sure to order the Gourmet Mix, which is half caramel glazed, and half CheeseCorn flavor. Simply delicious!
11. Explore Lower Wacker Drive
Have you ever seen “The Dark Knight”? If you have, I’m sure you remember this seen where the joker pulled a bazooka. Well, it was filmed on Lower Wacker Drive. If you get a chance, walk down there or drive, just check it out because it’s like seeing the basement of downtown.
The entire Wacker Drive system has three levels, with Lower Wacker being the middle layer. The lowest level, Lower Lower Wacker, is used for utilities and city storage. It’s also a shortcut to avoid downtown traffic, with the main stretch going from around Streeterville to the Financial District. Parts of it are also walkable.
EXTRAS EXTRAS EXTRAS
- Adler Planetarium Skyline Walk – this is the best view of the entire Chicago skyline. GO AT NIGHT! 13 more great views here https://360chicago.com/things-to-do/13-best-views-chicago-skyline
- Explore Little India, a 15 block stretch down Devon Avenue on the far north side of the city
