Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,809 reviews)
Oct 4 - Oct 7
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $669, price is now $423 per person
$423
per person
found 1 day ago
Queen is very small but nice staff
Reviewed on Jul 16, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,586 reviews)
Oct 4 - Oct 7
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $795, price is now $457 per person
$457
per person
found 1 day ago
Outstanding breakfast and one of the nicer traveling experiences I've had in a while. Big Europe vibes (but with AC!) Highly recommend!
Reviewed on Jul 16, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,136 reviews)
Aug 30 - Sep 5
6 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,693, price is now $1,095 per person
$1,095
per person
found 1 day ago
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy.
As is all of Chicago.
Trying to sell in room soap products for exorbitant prices tachy as hell.
Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.
Reviewed on Jul 14, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,566 reviews)
Oct 4 - Oct 7
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $779, price is now $509 per person
$509
per person
found 1 day ago
Top rated hotels for your Chicago vacation package
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
$169 nightly
The price is $193 total per night
$193 total
Aug 3 - Aug 4
Total with taxes and fees
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and a microwave in a common area.
Free airport shuttle
Pet friendly
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
$190 nightly
The price is $226 total per night
$226 total
Jul 19 - Jul 20
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 75 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 banquet hall.
Pet friendly
Free WiFi
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.98 mi from city center
$299 nightly
The price is $355 total per night
$355 total
Jul 19 - Jul 20
Total with taxes and fees
Guests of Omni Chicago Hotel have access to a 24-hour gym, in-room fitness, and free WiFi in public areas. Valet parking is offered for USD 89.49 per night. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include conference space, express check-out, and a porter/bellhop.
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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