Chicago Holiday Deals
Top hotels for your Chicago holiday
River Hotel
Reviewed on 23 Mar. 2025
Crowne Plaza Chicago West Loop by IHG
Reviewed on 22 Mar. 2025
Embassy Suites by Hilton Chicago Downtown River North
Reviewed on 24 Mar. 2025
Popular places to visit
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
McCormick Place
During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Recommended cities for you
- Anaheim Holidays
- Atlanta Holidays
- Atlantic City Holidays
- Austin Holidays
- Boston Holidays
- Charleston Holidays
- Charlotte Holidays
- Dallas Holidays
- Daytona Beach Holidays
- Denver Holidays
- Fort Lauderdale Holidays
- Fort Myers Holidays
- Grand Canyon Holidays
- Honolulu Holidays
- Houston Holidays
- Key West Holidays
- Las Vegas Holidays
- Los Angeles Holidays
- Miami Holidays
- Monterey Holidays
- Montreal Holidays
- Myrtle Beach Holidays
- Naples Holidays
- Nashville Holidays
- New Orleans Holidays
- New York Holidays
- Niagara Falls Holidays
- Ocean City Holidays
- Orlando Holidays
- Palm Springs Holidays
- Philadelphia Holidays
- Phoenix Holidays
- Portland Holidays
- Reno Holidays
- San Antonio Holidays
- San Diego Holidays
- San Francisco Holidays
- Sarasota Holidays
- Savannah Holidays
- Seattle Holidays
- Sedona Holidays
- St. Petersburg - Clearwater Holidays
- Tahoe City Holidays
- Tampa Holidays
- Toronto Holidays
- Vancouver Holidays
- Washington Holidays
Book your Chicago holiday package
Top picks
^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.