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! (3,991 reviews)
Jun 24 - Jun 26
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $686, price is now $438 per person
$438
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.0-star property
Wind Creek Southland Casino and Hotel
East Hazel Crest
9.4/10 Exceptional! (336 reviews)
Jun 17 - Jun 24
7 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 $1,032, price is now $643 per person
$643
per person
found 2 hours ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again
Reviewed on Nov 17, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,124 reviews)
Jul 8 - Jul 11
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $952, price is now $598 per person
$598
per person
found 1 day ago
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (455 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 $1,279, price is now $836 per person
$836
per person
found 1 day ago
5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
9.4/10 Exceptional! (1,002 reviews)
Jun 17 - Jun 24
7 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 $3,899, price is now $2,555 per person
$2,555
per person
found 2 hours 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 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
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
The price is $171 total per night
$171 total
per night
May 26 - May 27
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 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 conference space, a business center, and express check-in.
Pet friendly
Free WiFi
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
The price is $253 total per night
$253 total
per night
May 23 - May 24
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 securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
Pet friendly
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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