Famous for its stunning architecture, endless museums and deep-dish pizza, Chicago is rich in history and well-known all over the world.

It also makes for an awesome hotspot during the summer. However, the good weather is only around for 3 months of the year so you need to enjoy it while you can!

There are so many things you can do, from exploring the beautiful beaches and walkways to dining out at world-famous restaurants, giving you a taste of what the city has to offer.

But if you’re only there for a short stay, there are just some things that you cannot miss before you leave.

Here are 5 cool places in Chicago you should visit this summer.

1. The Beach

There’s no better place to visit in Chicago when the sun comes out. Soak up the glorious sunshine at one of the many beaches around the city. Whether it’s to explore, relax or catching a tan, you will have an awesome time. Make sure you pack a swimsuit too for a dip in the ocean.

One of the best beaches to go to is Oak Street Beach. It’s one of the most popular destinations for sunbathing due its amazing view of the skyline. If you’re a fan of volleyball, there are plenty of chances to take part too. But before you arrive, stop by Jeff Zimmermann’s mural by the underpass for a cool photo opportunity.

Another great beach is Rainbow Beach Park. It is located next to Rainbow Beach Victory Garden, one of the oldest public gardens in Chicago. For any of you that loves wildlife, head towards the north and explore Rainbow Beach Dunes for a chance to see some of the area’s native creatures.

2. Music Festivals

Summer weekends in Chicago often mean one thing: music festivals. Everywhere you look, you will have plenty of opportunities to enjoy live music, no matter your taste. Join the hordes or experience VIP; either way, you’re going to have an amazing time. Everyone will be signing their heart’s out so don’t hold back.

One of the most famous music festivals in Chicago is Lollapalooza. Head to Grand Park between August 1-4 and see some of the world’s biggest artists shut the place down. Purchase a day ticket for a great day’s entertainment or a weekend pass for the ultimate experience.

For those of you that prefer rock to pop, Ravinia Festival at Highland Park runs all summer with artists scheduled for every day. Bring your own food, drink and deck chair for day of awesome music.

If you would prefer to stay away from the masses and but want the festival experience, there are lots of street music spots that crop up all over town so you’ll never go without.

3. Rooftop Bars

Nothing quite says summer vibes than an exotic cocktail or cold glass of beer. The Chicago skyline makes for an awesome backdrop so make sure you head to one of the many rooftop bars this summer. Once you’ve done it, there’s no way you’d come back to Chicago without stopping for a drink above the city streets!

If you are looking to try something new, a cool place to go this summer is Cindy’s. It’s a rooftop bar and restaurant at the Chicago Athletic Association Hotel and offers some of the best views in the city. See Millenium Park like never before while sipping on a refreshing beverage.

For you wine lovers, make sure you stop by J. Parker. The views over Lincoln Park are nothing short of stunning and the music always proves a hit. If the day is particularly great, be sure to get there early though as many will have the exact same idea as you. If you do end up having to wait for a seat, you won’t be disappointed.

4. Boat Tours

Looking to escape the hustle and bustle of the city streets? If so, a boat tour across the river is the perfect solution. Here are three that are particularly great.

First comes the Sea Dog boat tour at Navy Pier. From adventurous speed boat adventures to classic Chicago architecture tours, they have it all. While you’re at Navy Pier, make sure you head to the Shakespeare Theatre – the shows aren’t expensive and you’ll have a great time.

Next comes the Chicago First Lady River Cruise. The tour lasts for 90 minutes and explores Chicago’s riverfront. When you purchase a ticket, you also get access to all the exhibitions at the Chicago Architecture Centre. If you plan on taking pictures while on the tour, there are versions of the tour that let you walk around the boat.

Finally, hop aboard the Odyssey Chicago River Dinner Cruise for a dinner with your other half. The cruise starts near the NBC tower and lasts for about 2.5 hours. Depending on when you travel, you may even see some fireworks. By the time it finishes, you’ll have finished a delicious three-course meal and been through a bottle of wine (or two).

5. Free Park Movies

Chicago Park District is the place to go to watch a movie outdoors. Pack a blanket, some snacks and you’re good to go. There are more than 200 movies scheduled all over the city, from the classics to modern day hits.

Here’s a small selection of movies you can watch this summer and where to watch them (here’s the full list):


  • Mary Poppins Returns (Sunday, June 23 at 8:30pm, Brooks Park)
  • Jurassic World: Fallen Kingdom (Tuesday, June 25 at 8:30pm, Hamilton Park)
  • Galaxy Quest (Wednesday, June 26 at 8:30pm, Lincoln Park)
  • Romeo + Juliet (Thursday, June 27 at 8:30pm, Wicker Park)
  • Black Panther (Thursday, June 27 at 8:30pm, Austin Town Hall Park)
  • Dirty Dancing (Friday, June 28 at 8:30pm, Portage Park)
  • Dunkirk (Sunday, June 30 at 8:30pm, Chicago Women’s Park and Gardens)


  • Grease (Monday, July 1 at 8:30pm, Burnham Park)
  • Jaws (Tuesday, July 2 at 8:30pm, Ridge Park)
  • Les Miserables (Thursday, July 11 at 8:15pm, Wicker Park)
  • Creed II (Friday, July 12 at 8:30pm, Moore Park)
  • The Incredibles 2 (Thursday, July 18 at 8:15pm , Commercial Club Park)
  • E.T. the Extra-Terrestrial (Saturday, July 20 at 8:15pm, Horner Park)
  • Dreamgirls (Monday, July 22 at 8:15pm, Harold Washington Park)


  • Jane Eyre (Thursday, Aug 1 at 8:15pm, Chicago Women’s Park and Gardens)
  • Jumanji: Welcome to the Jungle (Friday, Aug 9 at 8:15pm, Palmer Park)
  • Meet Me In St. Louis (Monday, Aug 12 at 8:15pm, Lincoln Park)
  • Footloose (Tuesday, Aug 13 8:15pm, Welles Park)
  • Avengers: Infinity War (Friday, Aug 16 at 8pm, Tilton Park)
  • Bohemian Rhapsody the Movie (Friday, Aug 16 at 8pm, Independence Park)
  • Moulin Rouge (Monday, Aug 19 at 8pm, Lincoln Park)
  • The Star (Friday, Aug 23 at 8pm, Shedd Park)
  • Spider-Man: Into the Spider-Verse (Saturday, Aug 24 at 7:37pm, Buttercup Park)
  • First Man (Saturday, Aug 24 at 8pm, Chicago Women’s Park and Gardens)
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