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June 24, 2023
Chicago, Illinois

Annie & James

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    Things To Do

Things To Do

Pizza Pizza!

No trip to Chicago is complete without trying the city's famous deep-dish pizza. Some popular spots to try include Lou Malnati's, Giordano's, and Pequod's. Our favorite thin crust pizzas can be found at...Bob's Pizza, Spacca Napoli (Ravenswood), Coda di Volpe (Lakeview), Piece Brewery (Wicker Park), Lou Malnati's, the list goes on...

Chicago Style Hot Dogs

100 West Ontario Street, Chicago, IL 60654

Another Chicago staple is the Chicago-style hot dog, which typically includes a steamed poppy seed bun, an all-beef hot dog, mustard, relish, onions, tomatoes, pickles, celery salt, and sport peppers. The best spot nearby is Portillo's.

Italian Beef

These sandwiches are made with thinly sliced beef, peppers, and a flavorful jus, and are a must-try in Chicago. Al's Beef, Johnnie's Beef, and Mr. Beef are all popular spots.

Grab a Burger

Our favorite quick burger is at Small Cheval. The original location is in Wicker Park, but the Old Town location is closest to where most guests will be staying. James’ favorite fancy sit-down burger is at Bavette’s, and if you’re going to Bavette’s, bring your appetite because you’ll have to get a steak too.

Starbucks Reserve Roastery

646 Michigan Avenue, Chicago, IL 60611

Four levels of java for the coffee lovers, right on Michigan Ave.

Bakeries!

Annie's favorite croissant in the downtown area is at Hendrickx Belgian Bakery (100 E Walton). Best slice of cake is the Princess Cake at Lost Larson, which you'd have to travel to Wicker Park or Andersonville for. Order ahead, they run out! For a trip down memory lane, visit the old fashioned american bakery that Annie worked at - Sweet Mandy B's (original, and best location is Lincoln Park, also has a location in Streeterville).

Oak Street Beach

Chicago, IL 60611

Hit the beach, take a walk along the waterfront, enjoy beautiful Lake Michigan!

Milton Lee Olive Park

East Ohio Street, Chicago, IL 60611

A nice park along the waterfront.

Chicago Architecture Center

111 East Wacker Drive, Chicago, IL 60601

We LOVE the architecture boat tour! Several companies offer tours along the river. Our favorites are Chicago Architecture Center and Architecture Tour Chicago.

Chicago Riverwalk

Chicago Riverwalk, Chicago, IL

Great for a pretty walk with snacks and beverages along the way.

The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603

So many great permanent exhibits. Special exhibits on our list to check out this June are the Van Gogh Avant Guard Exhibit and Ink Play: Paintings by Lui Shou-Kwan.

Museum Campus

Chicago, IL

Lots of great museums here - Shedd Aquarium, Adler Planetarium & Field Museum are here!

West Randolph Street

West Randolph Street, Chicago, IL

TONS of fabulous food spots can be found along and around Randolph street in the west loop. We love Publican Quality Meats, Green Street Smoked Meats, Au Cheval, Small Cheval, Duck Duck Goat, Cabra, and so many more...!

For all the days along the way
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