A long weekend in Chicago
- Jan 25
- 1 min read
Updated: Jan 26
In June, we'll be spending a long weekend in the famed Windy City. We arrive in the morning after an overnight flight. See the budget here.

Day 1
Morning: Drop luggage at the Hyatt Regency and grab breakfast at Eggy’s Diner. Riverwalk to Navy Pier and enjoy Lake Michigan.
Afternoon: Return to hotel and take a nap.
Evening: Chicago Architecture River Cruise at 6PM. Dinner at Lou Malnati’s Pizzeria. Watch the fireworks at Navy Pier at 10PM.
Day 2
Morning: Early morning sunrise walk to the Bean at 6AM. Breakfast at Wildberry. Walk around Millenium Park. Art Institute of Chicago. Pick up Portillo’s. Baseball Game at Wrigley Field.
Afternoon: Shop along the Magnificent Mile.
Evening: Eat dinner at Chicago Pizza and Oven Grinder Company.
Day 3
Morning: Breakfast at Lou Mitchell’s. Skydeck Chicago at Willis Tower. Frank Lloyd Wright house. Lunch at Hamburger University.
Afternoon: Field Museum.
Evening: Adler Planetarium at sunset. Dinner at MCCB in Chinatown and walk around.
Day 4
Morning: Eat at Al’s Italian Beef and last-minute shop along the Magnificent Mile.
Afternoon: Head to the Airport to catch our flight!
Looking for:
Best souvenirs.
Activities we should add or cut.


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