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
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (380 reviews)
Feb 13 - Feb 16
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $542, price is now $361 per person
$361
per person
found 18 hours ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,773 reviews)
Feb 27 - Mar 1
2 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $621, price is now $400 per person
$400
per person
found 20 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
4.0-star property
DoubleTree by Hilton Chicago - Alsip
8.2/10 Very Good! (1,007 reviews)
Feb 12 - Feb 18
6 night stay
Los Angeles (LAX) to Chicago (MDW)
Frontier Airlines • Non-stop • Coach
Chicago (MDW) to Los Angeles (LAX)
Delta • Non-stop • Coach
Save 100% on your flight
Price was $682, price is now $455 per person
$455
per person
found 1 day ago
Staff was friendly and organized, room was clean, quiet and comfortable,
Reviewed on Nov 17, 2025
5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
9.4/10 Exceptional! (1,000 reviews)
Feb 19 - Feb 24
5 night stay
San Juan (SJU) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to San Juan (SJU)
JetBlue Airways • Non-stop • Coach
Price was $1,628, price is now $1,113 per person
$1,113
per person
found 1 day ago
The entire experience was excellent!! Hotel was very clean and staff were so friendly and helpful. They try hard to make you feel welcome and help with anything you need. Restaurant has delicious food and again service is outstanding! Best experience at any place I have ever stayed.
Reviewed on Nov 20, 2025
4.0-star property
Hilton Orrington / Evanston
Downtown Evanston
7.6/10 Good! (1,002 reviews)
Feb 26 - Mar 3
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Los Angeles (LAX)
JetBlue Airways • Non-stop • Coach
Price was $683, price is now $476 per person
$476
per person
found 12 hours ago
Staff was very friendly and helpful. I left my pouch with my passport and phone in the limo that took me to the airport. I called the hotel and they contacted my friends who were still there and had them contact the limo driver who returned to the airport with the much needed pouch.
Reviewed on May 31, 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 $111 total per night
$111 total
per night
Dec 18 - Dec 19
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 luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.
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 $123 total per night
$123 total
per night
Dec 14 - Dec 15
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 securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and a porter/bellhop.
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
The price is $145 total per night
$145 total
per night
Dec 28 - Dec 29
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 securing valuables, concierge services, and access to locker space. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
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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