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 2 hours 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 15 - Jul 18
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,069, price is now $705 per person
$705
per person
found 19 hours ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,511 reviews)
Jul 27 - Jul 31
4 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,171, price is now $782 per person
$782
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 2026
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,011 reviews)
Aug 22 - Aug 29
7 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,804, price is now $1,272 per person
$1,272
per person
found 1 day ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!
Reviewed on Jul 8, 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
$140 nightly
The price is $167 total per night
$167 total
Jun 29 - Jun 30
Total with taxes and fees
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.
Free WiFi
Restaurant
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
1.07 mi from city center
$154 nightly
The price is $183 total per night
$183 total
Jun 28 - Jun 29
Total with taxes and fees
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 reception hall, wedding services, and a TV in a common area.
Pet friendly
Free WiFi
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$203 nightly
The price is $242 total per night
$242 total
Jun 30 - Jul 1
Total with taxes and fees
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.
Breakfast included
Free WiFi
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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