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Things To Do

The Art Institute of Chicago

The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603

Contains the largest collection of impressionist art outside of Europe. Ryan's favorite painting on display is "L'Estaque" by Émilie Charmy, and Jean-Paul loves "The Plan of Chicago, 1909: Chicago" by Daniel Hudson Burnham in the Architecture and Design wing.

Chicago Architecture Center

Chicago Architecture Center

111 East Wacker Drive, Chicago, IL 60601

One of the many museums of Chicago, Jean-Paul regularly volunteers here. The museum is small, and contains several exhibits. We recommend pairing a ticket with either an architecture boat tour through the museum, or a guided architecture walking tour.

Chicago River Architecture Boat Tour

Chicago River Architecture Boat Tour

112 E. Wacker Drive, Chicago, IL 60601

One activity we highly recommend is the architecture boat tour. There are several boat tours operators throughout Chicago, but our favorites are from the Chicago Architecture Center, Wendella, and Shoreline Sightseeing. Each tour is slightly different, but generally lasts 90 minutes along the main, north, and south branches of the Chicago river. All tours leave from slightly different locations along the river, so keep an eye out for that information on your ticket. If your docent happens to highlight 150 N Riverside (the tuning fork building with an extremely narrow base) - that is Ryan's office!

Chicago Riverwalk

Chicago Riverwalk

Chicago, IL 60601

The Chicago riverwalk is a roughly 1.25 mile path along the southern side of the main branch of the Chicago River. Opened in 2015, the riverwalk is a free, linear park perfect for leisure, snacks, and drinks. If you need a spot to rest with a cold beer, checkout our favorite riverfront spot, The Northman. Note - the Eastern end of the riverwalk connects with the Chicago Lakefront Trail.

Lakefront Trail

Lakefront Trail

Lakefront Trail, Chicago, IL

A popular free activity, the Lakeshore trail extends 18.5 miles along the edge of Chicago’s shoreline with Lake Michigan. The trail is connected to bird sanctuaries, parks, beaches, concrete piers and offers opportunity to walk, jog, cycle, and more. Please note - there are specific entrances and bridges to get to the lakeshore trail. Do not cross Lake Shore Drive unless you are at a crosswalk.

360 Overlook/Skydeck

360 Overlook/Skydeck

875 N. Michigan Avenue, Chicago, IL 60611

The 360 Chicago (Located in Ryan and Jean-Paul’s building) or the Skydeck (located in the Sears Tower) offer panoramic views of Chicago. We are partial to the 360 Chicago experience, but both offer spectacular views of the city. Please note - the best time to see the views are during the day until sunset. Chicago dims it’s lights during the summer as it lies along a migratory bird path, so at night you won’t see as much as you think.

Field Museum

Field Museum

1400 South Lake Shore Drive, Chicago, IL 60605

The Field Museum is renowned for its collection of artifacts and specimens. Its most famous resident is Sue, the largest, most complete, and best-preserved Tyrannosaurus Rex ever discovered. Located in Chicago's Museum Campus area.

Griffin Museum of Science and Industry

Griffin Museum of Science and Industry

5700 South DuSable Lake Shore Drive, Chicago, IL 60637

Located further south in Hyde Park, adjacent to the University of Chicago’s main campus and the Obama presidential library, lies the Museum of Science and Industry (one of the few preserved buildings from the 1898 Word’s Fair). We recommend taking an Uber/Lyft to this location. The museum takes about 2-3 hours to see, special exhibits take longer, but we recommend buying the special tickets that include a guided tour of a U-Boat captured during World War II, located in the basement of the building.

Lou Malnati's Pizzeria - Gold Coast Location

Lou Malnati's Pizzeria - Gold Coast Location

1120 North State Street, Chicago, IL 60610

Deep Dish is a unique Chicago style pizza that we recommend people try - especially if it is your first time in the city! Please note that you should make reservations well in advance as deep dish is popular. It usually takes about 40-60 minutes to bake the pie once you are seated, so plan for time!

Jeni's Splendid Ice Creams

Jeni's Splendid Ice Creams

871 North Wabash Avenue, Chicago, IL 60611

Our favorite summer ice cream spot. Jeni's is a short walk from the Gold Coast triangle hotels (The Thompson, Viceroy, etc.). It is also just two blocks away from our favorite park to people watch, Washington Square Park.