Chicago Vacation Packages
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4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,438 reviews)
Apr 19 - Apr 21
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Price was $398, price is now $265 per person
$265
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (441 reviews)
Jun 4 - Jun 8
4 night stay
New York (JFK) to Chicago (ORD)
JetBlue Airways • Coach
Chicago (ORD) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $1,638, price is now $1,024 per person
$1,024
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
JW Marriott Chicago
Downtown Chicago
9.2/10 Wonderful! (1,007 reviews)
Apr 30 - May 2
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $681, price is now $448 per person
$448
per person
found 1 day ago
Loved how close the property is to union station and walkable to magnificent mile of shopping/dining and millennium park.
Reviewed on Dec 30, 2024
3.0-star property
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
8.8/10 Excellent! (1,873 reviews)
Jun 4 - Jun 7
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Delta • Coach
Save 100% on your flight
Price was $1,264, price is now $881 per person
$881
per person
found 1 day ago
Very nice room, super clean, friendly staff, great location
Reviewed on Feb 18, 2026
3.5-star property
Hotel Indigo Chicago-Vernon Hills by IHG
8.4/10 Very Good! (1,009 reviews)
May 23 - May 30
7 night stay
New York (NYC) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to New York (NYC)
Spirit Airlines • Coach
Save 100% on your flight
Price was $726, price is now $536 per person
$536
per person
found 1 day ago
A very nice hotel! Staff was great, helpful and respectful.
Reviewed on Aug 2, 2025
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 $121 total per night
$121 total
per night
Apr 1 - Apr 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 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
The price is $179 total per night
$179 total
per night
Apr 6 - Apr 7
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.
Breakfast included
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
0.83 mi from city center
The price is $153 total per night
$153 total
per night
Mar 23 - Mar 24
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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