Chicago Vacation Packages
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4.0-star property
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
8.4/10 Very Good! (2,006 reviews)
Oct 1 - Oct 4
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Price was $921, price is now $648 per person
$648
per person
found 1 day ago
The rooms are excessively small, but they are clean.
Reviewed on Jul 8, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (497 reviews)
Sep 17 - Sep 20
3 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,457, price is now $956 per person
$956
per person
found 1 day ago
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,586 reviews)
Oct 1 - Oct 4
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,005, price is now $687 per person
$687
per person
found 1 day ago
Staff were helpful and courteous. Breakfast was the best I have exer experienced...and no cost! Location was perfect! Rooftop was spectacular!
Reviewed on Jul 9, 2026
4.5-star property
Omni Chicago Hotel
Downtown Chicago
9.2/10 Wonderful! (1,819 reviews)
Oct 1 - Oct 4
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Price was $977, price is now $696 per person
$696
per person
found 1 day ago
The room was amazing! It was spacious and clean. The staff were helpful and very considerate.
The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances.
Reviewed on Jul 8, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,136 reviews)
Sep 22 - Sep 25
3 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,637, price is now $1,171 per person
$1,171
per person
found 1 day ago
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.
Reviewed on Jul 8, 2026
Top rated hotels for your Chicago vacation package
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.98 mi from city center
$243 nightly
The price is $289 total per night
$289 total
Aug 9 - Aug 10
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
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
$163 nightly
The price is $193 total per night
$193 total
Jul 27 - Jul 28
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$206 nightly
The price is $245 total per night
$245 total
Aug 6 - Aug 7
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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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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