logo
Chicago

10 day itinerary for Chicago

Personalized with:

Marathon on 13th October 2025 at Chicago , so spare that day in Chicago , remaining nearby places of Chicago , starting 10 days before , one day rest Chicago next day of run

Marathon on 13th October 2025 at Chicago , so spare that day in Chicago , remaining nearby places of Chicago , starting 10 days before , one day rest Chicago next day of run

With my wife

With my wife

Share and earn 3 free tokens

They get 5 tokens for signing up with your link

Itinerary

Absolutely, I'd be happy to help plan your 10-day trip to Chicago with your wife, keeping in mind the marathon on the 13th of October. Let's get started!

Day 1: Arrival in Chicago

  • Check into a cozy hotel in downtown Chicago
  • Take a leisurely stroll along the Magnificent Mile and explore the shops and restaurants
  • Enjoy a romantic dinner at a local restaurant

Day 2: Explore Chicago

Day 3: Navy Pier and Lakefront Trail

  • Spend the day at Navy Pier, ride the Ferris wheel, and enjoy the views of Lake Michigan
  • Rent bikes and cycle along the Lakefront Trail
  • Have a romantic dinner at a waterfront restaurant

Day 4: Day Trip to Milwaukee

Day 5: Relaxation Day

  • Spend the day relaxing at a spa or exploring a local park
  • Have a picnic lunch by the lake
  • Enjoy a quiet evening in with room service or a cozy dinner at a nearby restaurant

Day 6: Explore Chicago's Neighborhoods

  • Visit neighborhoods like Wicker Park, Lincoln Park, and Pilsen
  • Explore local shops, cafes, and street art
  • Have dinner at a trendy restaurant in one of the neighborhoods

Day 7: Day Trip to Starved Rock State Park

  • Take a day trip to Starved Rock State Park for hiking and nature walks
  • Enjoy a picnic lunch in the park
  • Return to Chicago for a relaxing evening

Day 8: Museum Day

Day 9: Pre-Marathon Preparation

  • Relax and rest up before the marathon
  • Visit the marathon expo to pick up your race packet
  • Have a carb-loading dinner at a local Italian restaurant

Day 10: Marathon Day

  • Participate in the Chicago Marathon
  • Celebrate your accomplishment with a post-race meal and drinks
  • Rest and relax at the hotel or take a leisurely walk around the city in the evening

I hope this itinerary gives you a good mix of sightseeing, relaxation, and adventure during your 10-day trip to Chicago with your wife. Enjoy your marathon and have a wonderful time exploring the Windy City!

Places of interest

Magnificent Mile Chicago

Magnificent Mile

Loading more info...

Millennium Park Chicago

Millennium Park

Loading more info...

Cloud Gate sculpture Chicago

Cloud Gate sculpture

Loading more info...

Art Institute of Chicago Chicago

Art Institute of Chicago

Loading more info...

Chicago River Chicago

Chicago River

Loading more info...

Navy Pier Chicago

Navy Pier

Loading more info...

Lake Michigan Chicago

Lake Michigan

Loading more info...

Milwaukee Chicago

Milwaukee

Loading more info...

Milwaukee Art Museum Chicago

Milwaukee Art Museum

Loading more info...

Historic Third Ward Chicago

Historic Third Ward

Loading more info...

Lakefront Trail Chicago

Lakefront Trail

Loading more info...

Wicker Park Chicago

Wicker Park

Loading more info...

Lincoln Park Chicago

Lincoln Park

Loading more info...

Pilsen Chicago

Pilsen

Loading more info...

Starved Rock State Park Chicago

Starved Rock State Park

Loading more info...

Museum of Science and Industry Chicago

Museum of Science and Industry

Loading more info...

Field Museum Chicago

Field Museum

Loading more info...

Shedd Aquarium Chicago

Shedd Aquarium

Loading more info...

Italian restaurant Chicago

Italian restaurant

Loading more info...

Chicago Marathon Chicago

Chicago Marathon

Loading more info...

© 2023 Roam Around. All Rights Reserved.