Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
DoubleTree by Hilton Chicago Schaumburg
7.4/10 Good! (1,006 reviews)
May 29 - Jun 3
5 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
It was close to Convention center and Woodfield mall
Reviewed on Sep 4, 2024
4.5-star property
Swissotel - Chicago
Downtown Chicago
8.8/10 Excellent! (1,967 reviews)
Jun 12 - Jun 16
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Spirit Airlines • Coach
per person
found 1 day ago
Had an amazing stay beautiful hotel
Reviewed on Feb 16, 2025
3.0-star property
Hyatt Place Chicago/Hoffman Estates
8.6/10 Excellent! (1,006 reviews)
May 29 - Jun 3
5 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
i booked this for my father and he raved about the staff, comfort, and ease of location
Reviewed on May 26, 2024
4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
8/10 Very Good! (2,043 reviews)
May 29 - Jun 3
5 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
The staff was were nice and welcoming. The bar/restaurant was very dated, as well as the rooms.
Although, it was convenient to an early flight out of O'Hare.
Reviewed on Mar 13, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,001 reviews)
Jun 12 - Jun 16
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Atlanta (ATL)
Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
Top rated hotels for your Chicago vacation package
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
The price is $128 per night
$128
per night
Mar 23 - Mar 24
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 53 per night. The front desk is staffed 24/7 to help with dry cleaning/laundry, concierge services, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi
L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.42 mi from city center
The price is $191 per night
$191
per night
Mar 20 - Mar 21
L7 Chicago by LOTTE features a 24-hour gym, free WiFi in public areas, and coffee in a common area. Valet parking is available for USD 64 per day. The front desk has multilingual staff on hand 24/7 to help with concierge services, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this boutique hotel include express check-in, free newspapers, and laundry facilities.
Pet friendly
Free WiFi
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 $150 per night
$150
per night
Mar 28 - Mar 29
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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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.
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