
Chicago Vacation Packages
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2.5-star property
Hampton Inn Chicago-Carol Stream
8.2/10 Very Good! (1,009 reviews)
Oct 27 - Nov 1
5 night stay
Nashville (BNA) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Nashville (BNA)
United • Coach
Save 100% on your flight
per person
found 14 hours ago
Lobby & elevators need an update. Room was probably renovated & was fine. Air conditioner a little tricky to keep at a regulated temperature.
Reviewed on Jul 4, 2025

4.0-star property
La Banque Hotel
9.4/10 Exceptional! (431 reviews)
Nov 7 - Nov 12
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Los Angeles (LAX)
Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,679 reviews)
Oct 3 - Oct 5
2 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I recently stayed at the Trump International Hotel & Tower Chicago, and it exceeded every expectation. From the moment I arrived, I was impressed by the warmth and professionalism of the staff. Check-in was smooth and welcoming, and I was personally escorted to my room—which turned out to be nothing short of spectacular.
The room itself was spacious, immaculately clean, and beautifully designed with modern touches and classic elegance. Floor-to-ceiling windows offered breathtaking views of the Chicago River and city skyline. The kitchenette was a nice bonus and made the room feel more like a luxury apartment than a typical hotel room.
The service throughout my stay was consistently excellent—attentive without being overbearing. Every request was handled promptly and with a smile, and it was clear that the staff genuinely cared about making my stay enjoyable.
I also had the chance to dine at Rebar, and the food and views were equally impressive. The atmosphere was relaxed yet refined, and it made for a perfect evening.
The location is ideal—walking distance to the Magnificent Mile, Millennium Park, and plenty of restaurants and shops. Despite being in the heart of downtown, the hotel felt like a peaceful retreat above the city.
Whether you're visiting Chicago for business or pleasure, I highly recommend the Trump International Hotel. It’s a standout experience in every way—luxury, location, service, and comfort all rolled into one.
Reviewed on Aug 14, 2025

3.0-star property
Four Points by Sheraton Chicago Schaumburg
8.8/10 Excellent! (295 reviews)
Oct 27 - Nov 1
5 night stay
Nashville (BNA) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Nashville (BNA)
United • Coach
Save 100% on your flight
per person
found 14 hours ago
Great location close to Woodfield Mall, shops and restaurants. This is our second stay here and we will be back again!
Reviewed on May 15, 2023
Top rated hotels for your Chicago vacation package

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$161 nightly
The price is $189 total per night
$189 total
Sep 1 - Sep 2
Total includes 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

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$198 nightly
The price is $229 total per night
$229 total
Sep 4 - Sep 5
Total includes taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.75 mi from city center
$152 nightly
The price is $179 total per night
$179 total
Aug 25 - Aug 26
Total includes taxes and fees
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include meeting rooms, express check-out, and a banquet hall.
Pool
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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