Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
8.8/10 Excellent! (2,013 reviews)
Oct 29 - Nov 4
6 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $859, price is now $581 per person
$581
per person
found 1 day ago
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (561 reviews)
Oct 22 - Oct 26
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 $1,322, price is now $808 per person
$808
per person
found 1 day ago
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!
Reviewed on Sep 21, 2026
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (3,012 reviews)
Oct 22 - Oct 26
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 $925, price is now $622 per person
$622
per person
found 1 day ago
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,077 reviews)
Oct 22 - Oct 26
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 $1,213, price is now $827 per person
$827
per person
found 1 day ago
Great view. There is a Nespresso machine!
Reviewed on Sep 21, 2026
4.0-star property
Stay One Chicago
Downtown Chicago
7.8/10 Good! (12 reviews)
Oct 22 - Oct 26
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 $1,607, price is now $1,103 per person
$1,103
per person
found 1 day ago
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!
Reviewed on Sep 20, 2026
Top rated hotels for your Chicago vacation package
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$179 nightly
The price is $213 total per night
$213 total
Sep 27 - Sep 28
Total with taxes and fees
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 luggage storage, securing valuables, and concierge services. 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$201 nightly
The price is $239 total per night
$239 total
Sep 27 - Sep 28
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 securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$179 nightly
The price is $213 total per night
$213 total
Oct 13 - Oct 14
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 82 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a fireplace in the lobby.
Pet friendly
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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