Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.5-star property
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
8.6/10 Excellent! (2,765 reviews)
May 23 - May 26
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $483, price is now $322 per person
$322
per person
found 1 day ago
Good room. Nice ionized water on every floor.
They should provide proper down comforters instead of just thick sheets. I was shivering all night.
Reviewed on Jan 15, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (441 reviews)
Jun 4 - Jun 8
4 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,458, price is now $896 per person
$896
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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,613 reviews)
May 25 - May 29
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,135, price is now $727 per person
$727
per person
found 1 day ago
Everything was perfect
Reviewed on Mar 9, 2026
4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
8.4/10 Very Good! (2,231 reviews)
May 23 - May 26
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $636, price is now $430 per person
$430
per person
found 1 day ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.
Reviewed on Feb 25, 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
$101 nightly
The price is $118 total per night
$118 total
Apr 1 - Apr 2
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 concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$156 nightly
The price is $183 total per night
$183 total
Mar 30 - Mar 31
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 luggage storage, dry cleaning/laundry, and concierge services.
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$129 nightly
The price is $151 total per night
$151 total
Mar 15 - Mar 16
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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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