Top 10 Things To Do In Chicago

and not feel like a tourist

Get off the couch and visit the Windy City…

in the summer…

Yeah, I’m not going to lie. Chicago is COLD in the Winter. Its still a great city to visit in January…but in the Summer…Chicago is really one of the coolest cities in the country! Midwestern hospitality, culinary expertise, sports mania, shopping galore, and the best damn architecture around makes this city such a fun destination! You will love it! But I am a little biased- I grew up here! So the Top 10 Things To Do in the city are from the perspective of a longtime residents. The list is far from complete- but my Pepper and I can give you suggestions on what WE enjoy doing, and think you might too! Email us if you need suggestions on other things that you enjoy.

1. Go to a Cubs Game

Even if you are not a baseball fan, Wrigley Field and its surrounding neighborhood are pretty cool to experience. Wrigley Field first opened in 1914, the oldest park in the National League. The red marquee over the main entrance, the ivy covered outfield wall, and the hand-turned scoreboard make this a special place for sports enthusiasts, outdoor lovers, and beer drinkers! “Wrigleyville” is a lively neighborhood loaded with bars, restaurants, and people. Vines, on Clark Street, is one of my favorite spots for a pre-game beer. Stick around the neighborhood after the game to take in all the drunken fans celebrating a win! Its a people-watching extravaganza!

If you visit Chicago in the Winter- Wrigleyville turns into a Holiday Bar Hop Haven! The Sports Bars turn into holiday themed bars (such as one of my faves, Elf’d Up, on Clark Street). Its a great time bar hopping from one Christmas theme to the next. Be prepared to pay a hefty cover at some bars who really do-it-up in Wrigley. Or, kick it old-school with those of us who have lived here for a while and head to Butch McGuires on Division Street for the Christmas madness there. A $5 cover gets you into the original Christmas-themed Classic bar.

2. Hit a street festival

Chicago is world renowned for its street parties celebrating culture, music and neighborhoods. If you have a chance to get out of the Gold Coast (where every tourist heads to) and check out one of the neighborhood festivals, you won’t regret it. Think local beer, live music, top-notch artists, street vendors, and one big, giant outdoor party! My personal favorite is Well Street Art Festival in June. Head there in the afternoon to check out the artists on display, but stay for the party that starts rocking about 4pm. For some serious people watching, PrideFest is the weekend AFTER Wells Street- come prepared for a good time!

3. Run/bike on the lakefront

The Chicago Lakefront is 18 miles of beautiful waterfront running, biking, walking, whatever! Rent a bike, go paddle boarding, have drinks at a beachfront restaurant, or just relax on a grassy knoll. Spending time on Lake Michigan is my own personal moment of zen. Head to Oak Street Beach to play volleyball or grab a bite to eat. Rent a SUP, take a yoga class or grab a beer at the beachfront restaurant shaped like a boat at North Avenue Beach. Montrose Beach, on the north side of the city, is my personal favorite. Its much more low key and not as crowded as the other beaches. The Dock, the beachfront restaurant there, has live music and a great bar scene at night. You can rent kayaks, SUP, or do yoga here too.

4. Have drinks on the River Walk

The River Walk is a mecca of restaurants and bars along the Chicago River Its super fun in the summer! Grab a beer and chill out as you watch the boats go by. Check out City Winery for a great social scene…It is CRAAAAAZY when the sun is shining. For a more sophisticated experience, RPM Seafood offers great food, great people watching, and patio seating on the river for a few extra bucks.

5. Dinner at a waterfront restaurant (other than the river)

Chicago isn’t exactly known as a tropical paradise, right? But, the city does have some pretty cool waterfront restaurants that are worth checking out. Ohio Street Beach has a charming outdoor cafe, Caffe’ Oliva. It sits right on the beach, just north of Navy Pier. You can sit and watch the triathletes as they train in Lake Michigan along the 1/2 mile wall that runs along the lake. Or just watch the waves roll in on the beach. If you are looking for more upscale dining on the lake try out The Lakefront Restaurant, a little further north at Fullerton. It has a casual outdoor patio during the summer, but serves meal indoors all year round. You can get a great water view even if it is below zero outside!

Do you want to feel like a local? Grab an Uber and head to Montrose Beach and The Dock! Casual, beach attire is on tap along with micro-brews galore at this beachfront bar and restaurant. Stick around for the live music at night. Plan ahead and go on a Wednesday or Saturday, where you can watch the Navy Pier fireworks after dinner along Montrose Harbor. Fireworks typically start about 9:30pm.

My last recommendation is kind of random, but I love it there. The Waterfront is in Edgewater- waaaaaay north along the lake. (Its still in the city, just pretty far north along Lake Shore Drive.) The food is, by most standards, terrible- but the atmosphere is just wonderful! Live music plays on most nights as you sit, literally, right next to the water with your toes in the sand.

TIP: Depending on wether you are into dining outside or the newest, hottest restaurants in town, the most up-to-date info is available at Chicago Eater. Its the holy grail when it comes to the latest news on bar and restaurant openings in the city.

6. Visit the Bean and linger for longer

The Bean, or CloudGate, in Millennium Park, is one of the most popular tourist attractions in Chicago. I get it, its pretty cool to see. It is a huge stainless steel public sculpture by Sir Anish Kapoor. Be sure to take some crazy photos of your reflection on the surface. Just down the street at Michigan and Monroe is the Crown Fountain, 50ft. twin towers depicting actual Chicago Residents spitting out water onto the crowd!

When all those fun and games are done at the park, stroll across Michigan Avenue and head up to Cindy’s, for a birds-eye view of Millennium Park thirteen stories from above. Grab yourself some fabulous American food, a delicious drink, and enjoy the city that lays before you.

7. Walk around a neighborhood (instead of Michigan Avenue)

Most visitors to Chicago head to the Gold Coast to shop, River North to eat, and Lakeview to see the Cubs. If you have time and are interested to see where locals hang out, travel to some of the charming neighborhoods of Chicago and get a little local flavor! Fulton Market District is hot hot hot for dining, Logan Square is where the hipsters head to, Wicker Park/Bucktown has a cool vibe, and Old Town is right off the lake for a convenient stroll after a day at North Avenue Beach.

8. Picnic at Millenium Park

Millenium Park is totally cool to see in itself- but plan ahead and pack a picnic for a FREE concert or movie on the Great Lawn! If Chicago weather cooperates, it gets pretty crowded- so come early and claim your real estate.

9. Kayak the Chicago River

Rent a kayaks row your way down the river! I love being on the river in the evening- Look for the Navy Pier Fireworks Kayak at Urban Kayaks - and you will see the city by night as well as a fireworks show…from the water!

TIP: For a way cool experience, visit the city over St. Patricks Day. You can party till dawn at some of the many Irish Pubs here, then head to the river to kayak as they dye the water green before the parade!

10. See the city from the deck of a boat

There is nothing better than getting out on Lake Michigan in the summer. If you are not lucky enough to know someone on a boat floating in the Playpen at Ohio Street Beach, then head over to Navy Pier and get a ticket for The Sea Dog Extreme! Be prepared to get wet…really wet! Its a wild boat ride where the captain does donuts in Lake Michigan for the main purpose of soaking everyone on board! Bring some spare clothes, boating fans! Its loads of fun!