Chicago Vacation Packages
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4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (3,353 reviews)
Sep 25 - Sep 29
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
4.5-star property
Swissotel - Chicago
Downtown Chicago
8.8/10 Excellent! (2,274 reviews)
Sep 25 - Sep 29
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Clean and attentive staff
Reviewed on Jun 21, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,623 reviews)
Sep 25 - Sep 29
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!
Reviewed on Jun 16, 2025
4.0-star property
citizenM Chicago Downtown
Downtown Chicago
9.4/10 Exceptional! (3,222 reviews)
Sep 25 - Sep 29
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Nice, staff, good location
Reviewed on Jun 22, 2025
4.5-star property
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
9/10 Wonderful! (1,917 reviews)
Sep 25 - Sep 29
4 night stay
Austin (AUS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual.
Reviewed on Jun 24, 2025
Top rated hotels for your Chicago vacation package
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
0.75 mi from city center
The price is $300 total per night
$300 total
per night
Jul 6 - Jul 7
At InterContinental Chicago Magnificent Mile by IHG, guests enjoy an indoor pool, a gym, and a steam room. Valet parking is offered for USD 88 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include free WiFi in public areas, express check-out, and a reception hall.
Pool
Spa
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
The price is $168 total per night
$168 total
per night
Aug 5 - Aug 6
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 securing valuables, concierge services, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
The price is $198 total per night
$198 total
per night
Jul 6 - Jul 7
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Additional amenities include a business center, express check-out, and a banquet hall.
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.
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