Chicago Vacation Packages
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4.5-star property
The Talbott, Autograph Collection
Downtown Chicago
9.4/10 Exceptional! (112 reviews)
Jul 1 - Jul 4
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $768, price is now $513 per person
$513
per person
found 1 day ago
Always stay here never anywhere else we love it
Reviewed on Dec 30, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,070 reviews)
Jun 18 - Jun 22
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,599, price is now $980 per person
$980
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,478 reviews)
Jul 29 - Aug 2
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,938, price is now $1,240 per person
$1,240
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,863 reviews)
Jul 29 - Aug 3
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
JetBlue Airways • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,518, price is now $1,700 per person
$1,700
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
Top rated hotels for your Chicago vacation package
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.97 mi from city center
$124 nightly
The price is $148 total per night
$148 total
May 20 - May 21
Total with taxes and fees
Guests of Hotel Felix River North/Magnificent Mile enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 74 per day. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and securing valuables. Other amenities at this boutique hotel include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pet friendly
Free WiFi
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$135 nightly
The price is $161 total per night
$161 total
May 10 - May 11
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
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 $185 total per night
$185 total
May 27 - May 28
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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