A LOCAL’S GUIDE TO CHICAGO IN THE SUMMER

Chicago summer — the reason us locals put up with the long, harsh winters! While there’s plenty to do here at any time of year, the warm weather opens up opportunities to enjoy the incredible lakefront and outdoor spaces. Because I get asked for recommendations quite a bit, I’ve compiled a list that’ll help you check off some of the best ways to enjoy a Chicago summer.

Flying to Chicago? Check out some of my air travel tips I’ve learned as an airline employee.

1. Bike along the Lakefront Trail

The Chicago Lakefront Trail is an 18-mile path right along the shore of Lake Michigan that provides some of my favorite views of the city. You’ll probably see some bright blue bikes along the trail — these are from Chicago’s super affordable bike sharing system, Divvy. Grab a bike from one of the many Divvy stations near the trail and go for a ride! It’s just $3 for every 30 minutes or $15 for an entire day. Hop on the trail near Museum Campus (pictured above) for the best skyline views or start at Oak Street Beach and head north for a beachfront ride.

2. Hop on a water taxi to Chinatown

I always recommend getting out on the Chicago River for a unique perspective of the city. One of the most affordable ways to ride down the river is by water taxi — literally a bright yellow boat that connects several Chicago neighborhoods. Hop on at the Michigan Ave stop and ride down to Chinatown for lunch to feel like you’re visiting an entirely different city. There’s no need to spend a lot of time here, but it’s great for a quick stroll and some authentic food.

3. Take an architecture boat tour

Did you know Chicago is the birthplace of the skyscraper? It’s hard not to be in awe of the historic buildings that make up our skyline, but it’s even more memorable to learn about the stories behind them. Although a bit more touristy, I always jump at the chance to take friends on an architecture tour when they visit. I try to take at least one tour to learn about every city I travel to, and an architecture boat tour is the one in Chicago you shouldn’t miss.

4. Grab a drink on a rooftop

Summer in Chicago is rooftop season! Cindy’s and LondonHouse are two of the most popular downtown rooftop bars that offer perfectly Instagrammable views of the city. My recent favorite (and less-well known) is the J. Parker in Lincoln Park. Keep in mind that the rooftops have limited space, so stop by earlier in the day to avoid waiting in line.

Bonus: For a more unique rooftop experience, visit the Royal Palms Shuffleboard Club in the Bucktown neighborhood and head to the Lido Deck. I had no idea shuffleboard could be so fun (yes, the game elderly people play on cruises).

5. Catch a Cubs game at Wrigley Field

A Chicago summer isn’t complete without a trip to Wrigley Field. Even if you’re not a sports fan, the atmosphere in Wrigleyville on game day is worth the trip. There’s also plenty of local bars and rooftops surrounding the stadium, making it a great area to spend a night out in — especially after a Cubs win.

6. Spend the afternoon at the beach

Get your tan on and enjoy the nice weather at Oak Street or North Avenue Beach. North Ave offers kayak and stand-up paddle board rentals if you want to get out on the water (you can also rent kayaks on the Chicago River for a different view). There’s also some unique restaurants on the beachfront, like this bar-on-a-boat. Bet you didn’t know you could have a city and beach vacation all-in-one!

7. Watch the fireworks at Navy Pier

Every Wednesday and Saturday night from Memorial Day to Labor Day, you can catch the Navy Pier fireworks show. I recommend heading back to the beach for the best views or hopping on a late night boat cruise (my favorite option if you don’t mind spending a bit). You can find the exact fireworks schedule and all of your cruise options here.

8. Attend an outdoor concert or festival

No matter when you visit in the summer, there’s plenty going on to explore. Taste of Chicago, Lollapalooza, and the Air & Water Show are some of the most popular summer events, but a quick Google search for “Chicago events” will show you all of your options. Be sure to check out what concerts are happening at Huntington Bank Pavilion on Northerly Island — my favorite outdoor amphitheater with a nice skyline view. You can also catch some free music at Jay Pritzker Pavilion in Millennium Park.

Keep in mind — there are SO many more options of things to do in the city, but these are some of my favorites as a local. If it’s your first time visiting Chicago, don’t skip out on the touristy activities just because they’re “touristy” — they’re popular for a reason!

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Looking for more cities to explore? Check out some of my favorite travel destinations here!