Chicago Vacation Packages
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4.0-star property
Wind Creek Southland Casino and Hotel
East Hazel Crest
9.4/10 Exceptional! (391 reviews)
Jul 24 - Jul 28
4 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $792, price is now $556 per person
$556
per person
found 1 day ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again
Reviewed on Nov 17, 2025
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (478 reviews)
Jul 8 - Jul 12
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,600, price is now $1,025 per person
$1,025
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,121 reviews)
Jul 9 - Jul 15
6 night stay
Burbank (BUR) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Burbank (BUR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,023, price is now $1,315 per person
$1,315
per person
found 3 hours ago
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
9.2/10 Wonderful! (395 reviews)
Aug 9 - Aug 12
3 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $926, price is now $645 per person
$645
per person
found 1 day ago
Thoroughly enjoyed my stay. Definitely worth another stay.
Reviewed on Apr 14, 2026
2.0-star property
Dorothy's
Lakeview
8.6/10 Excellent! (131 reviews)
Jul 8 - Jul 12
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $805, price is now $564 per person
$564
per person
found 1 day ago
Inexpensive place for Chicago.
Reviewed on Apr 28, 2026
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 $183 total per night
$183 total
per night
Jul 1 - Jul 2
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 securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.07 mi from city center
The price is $183 total per night
$183 total
per night
Jun 28 - Jun 29
Guests of The Chicago Hotel Collection - Magnificent Mile enjoy features like a 24-hour gym, free WiFi in public areas, and express check-out. Self parking is available for USD 58 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Other amenities at this boutique hotel include a TV in a common area, wedding services, and a reception hall.
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
The price is $242 total per night
$242 total
per night
Jun 30 - Jul 1
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry.
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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