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My Chicago Summer Bucket List

I’ve visited Chicago in every season, but I feel like it’s the summer season I know least. If I had a few days to spend in Chicago in summer, and unlimited money, here are a few of the things I’d do.

Disclosure: This post is sponsored by Hotels.com. All thoughts, opinions and typos are my own.

Not everyone is comfortable traveling just yet, but if you are, please keep these recommendations in mind:

  • Review local health mandates before you arrive, plus double check the hours of places you want to visit. Stores and restaurants may have temporarily hours or temporarily closed.
  • Wear a face mask.
  • Pack hand sanitizer and wash your hands on a regular basis.
  • Book a hotel with free cancellation in case you need to change your plans at the last minute

Where to stay when visiting Chicago

Before I set out exploring the city, I’ll need a home base – a hotel with a prime location. In my previous visits to Chicago, it’s always been best to stay in a hotel in the downtown area.

Ideally, you’ll find one that’s within walking distance to restaurants, shops and an L Train stop. And since it’s summer, it wouldn’t hurt to look through the photos to find hotels with rooftop pools or restaurants.

Hit the Chicago beaches

The view from the patio at Castaways in Chicago.
Photo Courtesy of Choose Chicago and Castaways

There are a few beaches in Chicago to explore – Foster Beach, Ohio Beach, and Oak Street Beach stand out. But for a true bucket list experience, reserve a cabana at Shore Club Chicago on North Avenue Beach (opens May 22), or just have a frozen beverage and enjoy the view from the rooftop patio of Castaways

Twirl in the fountain at Millennium Park

You know Millennium Park, home to the iconic “Bean” sculpture and the ice skating rink in the winter? It also is home to Crown Fountain, an art installation that draws crowds in the summer. Ever since I saw a picture of it, I’ve wanted to be there. 

The fountain is actually two huge LED screens showing videos of faces and the faces spit the water out. So cool. I don’t care if there are only kids playing in it. I’m going to join them.

Spend a summer evening on a rooftop

Couples having drinks on the rooftop of the London House in Chicago
Photo courtesy Choose Chicago/Photo by Adam Alexander Photography

I imagine the view from a rooftop bar or restaurant in Chicago is unforgettable. Recommended places include the exquisite Cindy’s at the Chicago Athletic Association Hotel and London House Chicago Rooftop, with its views of Lake Michigan and the Magnificent Mile.

Celebrate the Fourth in Chicago

Photo courtesy Choose Chicago

I’ve celebrated St. Patrick’s Day in Chicago, and I visited during Christmas. So, I think it’s time to add a summer holiday to the list. And the city does the Fourth of July big!

There’s a fireworks show along the Lake Michigan shoreline. Maybe that’s how I should time my rooftop bar outing?

See an awesome concert – for free

Chicago draws major artists and if I’m in the city when one of my favorites is as well…well, I’ll buy a ticket. But, I saw a list of performers who’ve played at the free Millennium Park Summer Series and I’d be more than up to attend if someone like Aimee Mann or Youssou N’Dour.

Kayak the Windy City’s skyscraper canyon 

Kayakers on the Chicago River
Photo courtesy Choose Chicago/Photo by Graham Chapman

I’ve done the Architecture boat tour in Chicago so I feel like it’s time to level up. What’s a more unique way to sightsee in downtown than from a kayak on the Chicago River?

Go where the OG gangster went

I just want to step foot in the Green Mill, Al Capone’s famous, seedy stomping grounds. It’s still a jazz bar with cocktails, so if I’m going to be there, might as well swirl a drink to some good tunes.

Go to a only-in-Chicago kind of festival

Photo Courtesy of Choose Chicago and Special Events Management Photo Courtesy of Chinatown Summer Fair

There is no shortages of festivals in Chicago (in non-covid times, that is). A few that would make for epic summer experiences: the Chicago Craft Beer Festival; the Chinatown Summer Fair with a Lion Dance Procession and music; Randolph Street Market Festival; and the music festival, Lollapalooza in Grant Park – because, why not?

Related post: My favorite non-summer festival is not technically a festival. It’s the Christkindlmarket.

Try some amazing food

I’d love to try the 16-course menu at Oriole (though it’s currently closed as they expand the dining room). And then there’s the not-secret secret menu item at Sun Wah to order. It’s the multicourse Beijing duck dinner, carved tableside.

And being a summer bucket list, there has to be ice cream on here. I’ve heard about the Original Rainbow Cone, and I admit, I’m intrigued. It includes chocolate, strawberry, Palmer House (which is vanilla with cherries and walnuts), pistachio, and orange sherbet.

Related post: Have kids? Check out these Chicago restaurants that are great for families.

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