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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.


Cloudgate AKA The Bean
Cloudgate AKA The Bean

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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