
Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,914 reviews)
Jun 11 - Jun 16
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,517, price is now $883 per person
$883
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026

4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,280 reviews)
Jul 11 - Jul 16
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,945, price is now $1,167 per person
$1,167
per person
found 1 day ago
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026

4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,458 reviews)
Jul 11 - Jul 16
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,116, price is now $1,334 per person
$1,334
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,663 reviews)
Jul 11 - Jul 16
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,009, price is now $1,330 per person
$1,330
per person
found 1 day ago
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!
Reviewed on Mar 30, 2026

5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
9.4/10 Exceptional! (1,002 reviews)
Jul 11 - Jul 16
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,619, price is now $1,838 per person
$1,838
per person
found 1 day ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!
Reviewed on Dec 31, 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
The price is $148 total per night
$148 total
per night
May 25 - May 26
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 securing valuables, tours or tickets, and luggage storage. Other amenities at this boutique hotel include a 24-hour business center, coffee/tea in a common area, and express check-out.

River Hotel
75 East Wacker Drive Chicago IL
0.5 mi from city center
The price is $137 total per night
$137 total
per night
Apr 30 - May 1
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi

Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.19 mi from city center
The price is $138 total per night
$138 total
per night
May 25 - May 26
Guests of Club Quarters Hotel, Central Loop, Chicago enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a business center, coffee/tea in a common area, and a computer station.
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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