Chicago Vacation Packages
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4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,767 reviews)
Sep 3 - Sep 7
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $887, price is now $586 per person
$586
per person
found 1 day ago
Best vibe. In the mix!
Reviewed on May 2, 2026
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,034 reviews)
Sep 1 - Sep 5
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,199, price is now $741 per person
$741
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
2.5-star property
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Ashburn
6/10 (66 reviews)
Jul 28 - Aug 4
7 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,115, price is now $728 per person
$728
per person
found 7 hours ago
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,518 reviews)
Aug 6 - Aug 9
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,088, price is now $732 per person
$732
per person
found 1 day ago
The room was comfortable and clean. The lobby could stand a refresh.
Reviewed on Jun 19, 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
$136 nightly
The price is $162 total per night
$162 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 luggage storage. 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
$245 nightly
The price is $288 total per night
$288 total
Jul 18 - Jul 19
Total with taxes and fees
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, luggage storage, and securing valuables. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
Pet friendly
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.98 mi from city center
$174 nightly
The price is $207 total per night
$207 total
Jun 29 - Jun 30
Total with taxes and fees
Guests of Omni Chicago Hotel have access to a 24-hour gym, in-room fitness, and free WiFi in public areas. Valet parking is offered for USD 89.49 per night. The 24-hour front desk has staff standing by to help with tours or tickets, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include conference space, express check-out, and a gift shop.
Pet friendly
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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