Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (347 reviews)
Dec 4 - Dec 9
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Los Angeles (LAX)
United • Coach
Save 100% on your flight
Price was $924, price is now $543 per person
$543
per person
found 1 day ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates
Reviewed on Feb 16, 2024
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,001 reviews)
Dec 4 - Dec 9
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Los Angeles (LAX)
United • Coach
Save 100% on your flight
Price was $1,788, price is now $1,054 per person
$1,054
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)
Dec 8 - Dec 11
3 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,086, price is now $654 per person
$654
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
4.0-star property
Level Chicago - River North
Downtown Chicago
9/10 Wonderful! (679 reviews)
Nov 8 - Nov 15
7 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,240, price is now $855 per person
$855
per person
found 1 day ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!
Reviewed on Jul 8, 2024
4.5-star property
Virgin Hotels Chicago
Downtown Chicago
9.2/10 Wonderful! (1,358 reviews)
Dec 4 - Dec 9
5 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Los Angeles (LAX)
United • Coach
Save 100% on your flight
Price was $876, price is now $617 per person
$617
per person
found 1 day ago
Absolutely loved this property. Super convenient, the metro and train stations a very short walk away. Right by the bean and river north. Cafe and commons club were fantastic, service was great by all staff.
Reviewed on Apr 6, 2025
Top rated hotels for your Chicago vacation package
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
0.83 mi from city center
$176 nightly
The price is $207 total per night
$207 total
Sep 22 - Sep 23
Total with taxes and fees
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
$168 nightly
The price is $197 total per night
$197 total
Sep 22 - Sep 23
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 concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
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
$183 nightly
The price is $215 total per night
$215 total
Sep 22 - Sep 23
Total with 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 securing valuables, luggage storage, and tours or tickets. Additional amenities include meeting rooms, express check-out, and a porter/bellhop.
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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