Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Arlo Chicago
Downtown Chicago
9.2/10 Wonderful! (1,826 reviews)
Dec 4 - Dec 9
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Los Angeles (LAX)
American Airlines • Coach
Price was $680, price is now $507 per person
$507
per person
found 1 day ago
Fantastic stay, amazing location.
Reviewed on Jun 25, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,373 reviews)
Oct 24 - Oct 26
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,016, price is now $616 per person
$616
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,001 reviews)
Oct 24 - Oct 26
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,032, price is now $763 per person
$763
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,714 reviews)
Nov 28 - Nov 30
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $1,183, price is now $905 per person
$905
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
3.0-star property
Hyatt Place Chicago/ Schaumburg
8.6/10 Excellent! (1,010 reviews)
Oct 25 - Oct 31
6 night stay
New York (JFK) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $686, price is now $530 per person
$530
per person
found 15 hours ago
It was family trip to Chicago and we stayed 2 nights in this hotel. The staff were excellent , the room was clean, and the breakfast offered a great variety. It's was fantastic stay!".
Reviewed on Sep 5, 2025
Top rated hotels for your Chicago vacation package
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
The price is $204 total per night
$204 total
per night
Sep 22 - Sep 23
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
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 $197 total per night
$197 total
per night
Sep 22 - Sep 23
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 dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1 mi from city center
The price is $179 total per night
$179 total
per night
Sep 22 - Sep 23
At Warwick Allerton - Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 72 per day. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this family-friendly hotel include a conference center, a 24-hour business center, and a computer station.
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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