8 days in Chicago & Oak Park Itinerary

8 days in Chicago & Oak Park Itinerary

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Route & dates

8 days in Chicago & Oak Park Itinerary

Start: Chicago
1
Chicago
— 4 nights
Drive:  30​min
2
Oak Park
— 3 nights
Drive:  30​min
End: Chicago

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've added Oak Street Beach, Michigan Avenue Bridge, Chicago’s First Lady Cruises, and other attractions to your itinerary. Kids will enjoy Museum of Science and Industry and Chicago Children's Museum. There's much more to do: admire the masterpieces at The Art Institute of Chicago, admire the local landmark of Buckingham Fountain, laugh and play at Navy Pier, and get a new perspective on nature at Field Museum.

For where to stay, maps, more things to do, and tourist information, refer to the Chicago online sightseeing planner .

If you are flying in from Mexico, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. Expect a daytime high around 3°C in December, and nighttime lows around -3°C. Finish up your sightseeing early on the 2nd (Thu) so you can go by car to Oak Park.

Things to do in Chicago

Museums Childrens Museums Outdoors

Side Trip

Horseshoe Hammond
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Navy Pier ©
Navy Pier

3
nights
Oak Park

Oak Park ©
Oak Park is a village adjacent to the West Side of the city of Chicago in Cook County, Illinois, United States. Ernest Hemingway Birthplace has been added to your itinerary. Start off your visit on the 3rd (Fri): browse the exhibits of Ernest Hemingway Birthplace, then admire the landmark architecture of Frank Lloyd Wright Home and Studio, and then admire the striking features of Frank Lloyd Wright's Unity Temple. On your second day here, admire the natural beauty at Morton Arboretum, then steep yourself in history at Pleasant Home, and then have some family-friendly fun at LEGOLAND Discovery Center.

To find ratings, traveler tips, photos, and other tourist information, go to the Oak Park trip itinerary planning website .

Oak Park is just a stone's throw from Chicago. In January, daily temperatures in Oak Park can reach 0°C, while at night they dip to -9°C. Wrap up your sightseeing by early afternoon on the 5th (Sun) to allow enough time to drive back home.

Things to do in Oak Park

Historic Sites Fun & Games Parks

Side Trips

LEGOLAND Discovery Center, Morton Arboretum, Riverwalk Lot
Highlights from your plan
Frank Lloyd Wright Home and Studio ©
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
Frank Lloyd Wright's Unity Temple ©

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