Plan your Chicago holiday with Expedia
- Our 2020 bundled deals are currently unavailable, but you can now book our 2021 holiday packages deals. Buy your accommodation, flight or car together and get extra savings on your next trip!
- We have selected for you amazing deals on incredible hotels in Chicago. Have a look simply by using the search bar above.
- Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!
For more information, visit our COVID-19 information page.
Start browsing now!
*Some hotels require you to cancel at least 24-48 hours before check-in.
2021 Chicago holiday deals
Top flight + hotel deals in Chicago
Where to stay in Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
4.5/5Wonderful!(187 area reviews)
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like House of Blues Chicago and Chicago Riverwalk are major draws. Catch the metro at Chicago Station (Brown Line) or Merchandise Mart Station to see more of the city.
3/5(1 area review)
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Chicago Museum of Science and Industry and Robie House.
Top Hotel Deals
Reviewed on 20 Oct 2020
Reviewed on 19 Oct 2020
Top things to do in Chicago
360 CHICAGO Observation Deck (Hancock Center)
Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions
The Field Museum
Frequently asked questions
Does Expedia have holiday package deals to Chicago?
How much can I save with a Chicago holiday package?
Can I choose my airline with a Chicago Expedia holiday package?
Do I lose money if I change my mind after I have booked my Chicago holiday package?
What are the best places to visit in Chicago?
What are the most popular activities for a Chicago holiday?
- Small-Group Walking Craft Beer & Pizza Tour
- 1 Hour Walk-In Axe Throwing Experience Chicago (Lake View)
- Helicopter Flight at Night
- Secret Food Tours Chicago
- Chicago Modern Walking Tour
- Underground Donut Tour - Wicker Park Edition