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11 Awesome Things to Do In Chicago This Summer

Millennium Park Pritzker Pavilion

It's beginning to feel a lot like summer in Chicago. Streets are green, the lakefront trail is filling, and patios are open!

Now it's time to make the most of the months that make us stick it out through Chicago winters. Time is a-wasting people, so get out of your chairs and get out there, and don’t be afraid to try something new – Chicago is so much more than a beer in Wrigley’s bleachers.

Here's a look at what you have to check out this summer in the Windy City.

11 Awesome Things to Do In Chicago This Summer

Architecture Tour

The Chicago Architectural Foundation's riverboat architectural tour has been winning rave reviews for years as the best thing to do in Chicago, but here's the crazy thing – we think it's actually still under-rated! This 1.5 hour tour takes you down the river from the mouth at Navy Pier, under the bridges of downtown, and around the bend of the North and South Branch. You get a view of the city as you've never seen it before, and your guide will pack more expertise and history into 90 minutes than you would think possible.

This is a tour worth making a must-do on your list. You won't just learn what the buildings are, but you'll learn who designed them, the challenges in building them, and the legends that roam their halls. You'll start as a Chicago neophyte, and finish as an insider.

Air & Water Show

You may think the Chicago Air & Water Show (Aug. 15 & 16) is for kids, retired military, or airplane buffs, but it's far more than that.

If you can watch this show from the water you'll get a rare glimpse of a Great American city skyline dotted with the most impressive airplanes in the world. There's something special about seeing an F-16 rip in front of the Hancock Tower along the shoreline, then catching it's roar move in from behind. Even if you can't be on the shore or the water, it's best to know if the show is going on when you're in town, as it's not uncommon for vehicles to nearly swerve off the highway when a jet whips overhead in pre-show practice.

Wander Wicker Park

Wicker Park, Chicago's answer to Brooklyn is electric come summertime. You'll want to take a swing by for the array of great cocktail bars, a long list of amazing taco joints, and mostly - the people watching.

This neighborhood has welcomed amazing restaurants from top chefs (try XOCO, and try not to go back), stores from independent artists and designers, and the city’s favorite street-side patio at Big Star.

Run or Bike the Lakefront Trail

Nothing says summer in Chicago (not even Wrigley) like a trek down the Lakefront Trail. The lake to one shoulder, the city to the other, an unparalleled skyline before you.

Meet the Maker at the Renegade Craft Fair

No, don’t meet YOUR Maker. Meet the maker of the art.

The June 27 & 28 version of the Renegade Craft Fair is a two-for-one bonus deal, allowing you to check out one of the great bars and venue of the city and amazing artists. Held at the Hideout, the fair is a great place to find special gifts, meet artists, and enjoy a beautiful day.

Chicago Food Planet's Chinatown Food Tour

Ping Tom Park Chinatown Chicago

Chicago Food Planet’s Chinatown Food Tour is one of the hidden gems of Chicago. For $55, you get three hours of sampling in five of the best Chinese restaurants in the city, while getting a guided tour of how to dine the traditional manner and the history behind each of these great restaurants.

Plus, your guide is filled with area knowledge, filling you in on the history of Chinatown as you digest between stops and soak in this city within the city with stops at a Buddhist Temple, tea shop, specialty store, and the little-known but beautiful Ping Tom Park along the Chicago River. It's the best way to visit Chinatown!

Stroll Lincoln Park's Nature Boardwalk

Lincoln Park Nature Boardwalk

Just south of the Lincoln Park Zoo is a sneaky little spot many residents don’t even know about, the Nature Boardwalk. Stroll along the pond among the lily pads, grasses, and butterflies of this oasis in the city. In full bloom, this respite from city traffic provides a zen-like experience and some of the best photo ops in the city as you soak in the skyline from amidst an urban wilderness.

Step Aside into the Alfred Caldwell Lily Pond

Alfred Caldwell Lily Pond

Get even further removed from the city bustle by finding the Alfred Caldwell Lily Pond in Lincoln ParkThis tranquil spot, tucked just steps off of the buzz of Fullerton, instantly takes you to a calmer, quiet place you wouldn’t imagine in a metro area of 8 million people.

Stroll Lincoln Square

It’s a place most tourists don’t go unless they’re visiting friends there, but this northwest side neighborhood is one of the favorites of locals. An old German and Greek neighborhood retains much of that influence, with several of the best German restaurants in the city, like the Brauhaus in the center of the Square.

The Old Town Folk School is an amazing, intimate venue to catch renowned folk and Americana artists, and it’s neighborhood pubs often host local musicians on their way to and from classes at the school.

Half Acre Brewing Co. features Saturday tours, and their taproom is a must for beer lovers to sit and sample.

Catch the old men fighting over Bocce Ball in Welles Park, grab a craft cocktail at the sliver of a bar that is Tiny Lounge, and soak in the feel of an authentic Irish Pub at The Grafton.

And if you’re there on a hot summer day, make your way to Gene’s Sausage Shop in the Square proper. Head up the stairs, into the elevator, and stumble onto the rooftop bar, one of the great casual rooftops in Chicago. Grab a Stiegel (or something heavier if you prefer) and a sausage and tan your forehead. This, is Chicago summer.

Party in the Street

Square Roots Folk Fest Lincoln Square

No city on Earth does street festivals as often or as well as Chicago.

They come in waves every weekend, featuring amazing live music, DJs, and entertainers. It’s a chance to sample street food, meet people, and best of all, drink outside. You’ll love Midsommarfest in Andersonville, Wicker Park Fest, and Maifest in Lincoln Square, but it’s hard to go wrong with any of them.

BYOB to the Pritzker Pavilion

Pritzker Pavillion

The free concerts on Monday nights in June and July at the Pritzker Pavilion in Millennium Park are fantastic ways to catch big stars on an amazing stage FOR FREE! Plus, you can bring your own beer, wine, cheese and snacks. Do this. Please. If only to check out architect Frank Gehry’s otherworldly creation.

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