Chicago Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Sonesta Chicago O'Hare Airport Rosemont
O'Hare
8.6/10 Excellent! (1,573 reviews)
Nov 13 - Nov 16
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $407, price is now $296 per person
$296
per person
found 1 day ago
Great location and Amazing restaurant downstairs
Reviewed on Sep 21, 2025
5.0-star property
Art Villa
West Town
10/10 Exceptional! (2 reviews)
Dec 3 - Dec 8
5 night stay
Phoenix (PHX) to Chicago (ORD)
American Airlines • Non-stop • Coach
Chicago (ORD) to Phoenix (PHX)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,500, price is now $1,582 per person
$1,582
per person
found 1 day ago
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,716 reviews)
Nov 4 - Nov 6
2 night stay
Dallas (DFW) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $843, price is now $585 per person
$585
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,001 reviews)
Oct 23 - Oct 26
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Price was $1,372, price is now $990 per person
$990
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
The price is $197 total per night
$197 total
per night
Sep 22 - Sep 23
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
The price is $252 total per night
$252 total
per night
Oct 18 - Oct 19
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
Pet friendly
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.75 mi from city center
The price is $218 total per night
$218 total
per night
Oct 2 - Oct 3
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Additional amenities include meeting rooms, express check-out, and a porter/bellhop.
Pool
Pet friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More trip options
- Nearby Destinations
- Destinations similar to Chicago
- Best neighborhoods in Chicago
- More to explore for Chicago
- Top trending
- Book on Expedia
Top trending
Hotels
- Rosemont Hotels with Hot Tubs
- Hotels in Magnificent Mile
- Naperville Cheap Hotels
- Hotels closest to Grant Park
- Hotels closest to Michigan Avenue
- Rosemont Hotel Deals
- Oakbrook Terrace Hotels with Hot Tubs
- Hotels closest to Wintrust Arena
- Downtown Chicago Hotels with Balconies
- Hotels in The Loop
- Hotels closest to Wrigley Field
- Gurnee Waterpark Hotels & Resorts
- Gurnee Hotels with Hot Tubs
- Hotels closest to United Center
- Hotels in Downtown Chicago
- Downtown Chicago Hotels with Pool
- Hotels closest to McCormick Place
- Hotels closest to Soldier Field
- Hotels closest to Navy Pier
- Downtown Chicago Hotels with Free Parking
- Hotels closest to Six Flags Great America
- Schaumburg Hotels with Hot Tubs
Cars
Packages
- Hotels in Magnificent Mile
- Hotels near Art Institute of Chicago
- Visit Navy Pier
- Hotels near Michigan Avenue
- Cheap Hotels in Downtown Chicago
- Hotels near Chicago Theatre
- Luxury Hotels in Downtown Chicago
- Hotels near Millennium Park
- Hotels with Suites in Downtown Chicago
- Visit Art Institute of Chicago
- Chicago vacations
- Hotels near Chicago Riverwalk
- Hotels in Central Chicago
- Hotels in River North
- Hotels in Downtown Chicago
- Hotels near Navy Pier
- Hotels near Soldier Field
- Hotels near Chicago Union Station
- Hotels near Grant Park
- Hotels in The Loop
