10 Things To Do in Chicago This Summer

1. Take a riverboat architecture tour

Forget the tour busses and the walking tours of the city, see the true architectural splendor of this great city with a unique perspective by taking an hour-long tour down the 3 branches of the Chicago River. It is inexpensive and departs from Navy Pier, allowing you to spend some time either before, or after, riding on the giant Ferris Wheel or taking in the views of the magnificent skyline. I have gone with the Shoreline Sightseeing tours 3 times and highly recommend them.

Chicago architecture

2. Eat food that you can only REALLY get in Chicago

Chicago has MUCH more than hot dogs and pizza! Travel north from Chicago Ave. to Lawrence along Western Ave. for good, authentic, diverse and unique eats. This is typically where tourists don’t play, simply because they don’t know about it. Go on down to Pilsen (South of the loop at 18th and Racine) for some amazing Mexican food. Any little shop will do, you’ll get delicious and authentic Mexican there.

Of course, I would be remiss if I didn’t at least tell you where to get the best pizza. Lou Malnati’s and Giordano’s  are favorites with locations all over the Chicagoland area, and Pizano’s in the Loop, well, their deep dish is BOSS. For something REALLY unique though, go to the Chicago Pizza and Oven Grinder Co.  Located across the street from the site of the famous 1929 St. Valentine’s Day massacre, only here can you get an upside down pizza that is beyond delicious, and I mean ONLY here, their recipe is patented!

As for a Chicago style hot dog, there are a ton of great places to check out. Don’t fall for the touristy places that everybody tells you to go to. You would be surprised that the littlest hole in the wall places you discover that not only save you money but will give you food you will remember for the rest of your life. The best hot dog place I’ve ever been to is Franks N’ Dawgs, which will give you a savory gourmet hot dog unlike anything you’ve ever tasted.

Want to splurge and have a meal you’ll remember forever? Skip Charlie Trotters and head west to the molecular gastronomy restaurant, Moto, which will give you an amazing culinary experience in the West Loop. Be prepared to spend though, a 10 course dinner for 2 with wine pairings runs over $500.

3. Enjoy all the FREE activities!

There are an overabundance of fun and free things to do in Chicago over the summer: “Movies in the park” starting at sunset in Grant Park surrounds you with the beauty of Chicago, take a bike ride up the Lake Shore Bike Path OR walk along the lakefront from 3500 Recreation south to Navy Pier (It’s a hell of a great walk to see some of the most amazing skyline you have ever seen in your life), free monday night concerts at Millennium Park, Taylor street Italian fest, Division Street street cafes, Lincoln Park Farmer’s Market (or any farmer’s market should do), go north to Albion beach to enjoy some urban quiet. The FREE Lincoln Park Zoo is north of the downtown area..See more fun and free activities listed on the Chicago Summer Calendar I have posted below.  

Want more ideas? Check out the Chicago Summer Calendar and add to your Google calendar simply by clicking the Google+ button on the bottom.

[googleapps domain=”www” dir=”calendar/embed” query=”src=chicagosummercalendar%40gmail.com&ctz=America/Chicago” width=”800″ height=”600″ /]

4. See a comedy Show at Second City.

5. Have a drink above it all

Skip the Sears Tower (locals just will not call it the Willis Tower) and the fees of the observatory and go to the 95th floor of the John Hancock building on Michigan Avenue and have a cocktail in the Signature Room. This is a better view of the city and instead of buying a ticket, you can have a drink or appetizer instead. You CAN stay for dinner, however the food isn’t as good as places listed in #2, and is pretty pricey for what you get. If you want a great view outside, go to the Vertigo Skylounge which is at the rooftop of the Dana Hotel and Spa.

6. Catch a Baseball game

Go to a White Sox game! I know Wrigley Field is famous for its age, and its history of suck, but unless you are a 20 something looking to bar hop, Wrigley Field is the last place you want to be. U.S. Cellular Field is nicer, has fantastic stadium food (the smells are ridic!) and a beer garden. You can take the Red Line elevated train (the EL) for only $2.50 directly to the stadium at 35th street-Sox Park . If you drive, come early and TAILGATE in the parking lot. That’s right TAILGATE!

7. At some point, ride the EL

Commuters might disagree with me, but if you don’t live in a big city like Chicago, this is a cool experience. I suggest hopping the Blue Line north from the city to North Ave, or the California stop for some cool hole-in-the-wall places. Or, of course, take the red line to a baseball game.

The Chicago EL train is the best way to get around Chicago

8. Spend a day on the Museum Campus

Go to the Shedd Aquarium, say “Hi!” to the grouper and check out the jellyfish. Walk over to the Planetarium & learn how tiny we are in this vast universe. Stay outside take pictures of the best skyline view you will get of the Windy City. Spend time at the Field Museum checking out all the dinosaurs. Soldier Field is right there too, for all you football fans! If you can time it right, try to see a concert at the Charter One Pavilion at Northerly Island – by far the best venue to see a live show in the whole city.

View from the Adler Planetarium

9. People Watch at the beach

Castaways on North Ave beach is a great place to grab a snack, a drink, and watch some craziness around you. Take a dip in Lake Michigan, play some beach volleyball, or go for a walk down the lakefront path. Keep in mind this is a VERY crowded beach, if you are anything like me and prefer a more quiet and private beach, head north on the Red Line to the Loyola stop, and walk to the Albion street beach.

View from the Lake Shore Drive bike Path – Photo by Mara Borkowski

10. Check out the Chicago music scene

Specifically, the blues. If you can’t go to blues fest, check out Buddy Guy’s Legends, which has live blues 7 nights a week. You can see great live music pretty much any night at a variety of venues, just last week I wandered into Underground Wonder Bar and spent the night dancing away to great tunes with cool, chill, fun people.

Metro Mix provides good information on the music scene in Chicago – from every venue, free or otherwise, to the blow-out Lollapalooza music festival in August.

What are your favorite things to do in Chicago over the summer? Leave a comment about your travel (or local) experience in Chicago.

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3 responses to “10 Things To Do in Chicago This Summer

  1. I was just thinking about how badly I have wanted to try Chicago Pizza and Oven Grinder. Literally.. JUST thinking about it. I’m on this!

  2. I loved the night view from the observation deck of Big John. Great recommendation. Yet like with the CN Tower in Toronto, also at night, I was left wondering (as looked so far down on distant tiny major city below) are we meant to be way up here? Does it make sense to build so far up when there is so much space all around below? That high in the air just felt like a place we weren’t meant to be, there seemed to be some violation of the natural order, some over-extension of the human reach.

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