Chicago Vacation Packages
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4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,602 reviews)
Jan 22 - Jan 25
3 night stay
Mesa (AZA) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $402, price is now $226 per person
$226
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,110 reviews)
Jan 22 - Jan 25
3 night stay
Mesa (AZA) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $507, price is now $272 per person
$272
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,248 reviews)
Jan 22 - Jan 25
3 night stay
Mesa (AZA) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $511, price is now $289 per person
$289
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.
Reviewed on Jul 26, 2025
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (367 reviews)
Jan 22 - Jan 25
3 night stay
Mesa (AZA) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $533, price is now $301 per person
$301
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
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,761 reviews)
Jan 22 - Jan 25
3 night stay
Mesa (AZA) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $773, price is now $445 per person
$445
per person
found 1 day 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
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
$118 nightly
The price is $139 total per night
$139 total
Nov 23 - Nov 24
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 concierge services, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$110 nightly
The price is $129 total per night
$129 total
Nov 25 - Nov 26
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 securing valuables. 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
$102 nightly
The price is $120 total per night
$120 total
Nov 17 - Nov 18
Total with taxes and fees
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, dry cleaning/laundry, and luggage storage. Additional amenities include a business center, express check-out, and a porter/bellhop.
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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