Chicago Vacation Packages

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Hilton Orrington / Evanston
4.0-star property

Hilton Orrington / Evanston

Downtown Evanston
7.6/10 Good! (1,002 reviews)

Feb 13 - Feb 15

2 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $234, price is now $144 per person
$144
per person
found 1 day 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

The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago
9.2/10 Wonderful! (1,264 reviews)

Jan 5 - Jan 11

6 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Price was $1,123, price is now $565 per person
$565
per person
found 7 hours 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

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Downtown Chicago
9/10 Wonderful! (380 reviews)

Feb 13 - Feb 16

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $588, price is now $333 per person
$333
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3.0-star property

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

7.2/10 Good! (1,168 reviews)

Jan 20 - Jan 26

6 night stay

New York (JFK) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to New York (JFK)

Frontier Airlines • Coach
Save 100% on your flight
Price was $477, price is now $292 per person
$292
per person
found 3 hours ago
Very nice and helpful staff.

Reviewed on Nov 28, 2025

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0-star property

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
9/10 Wonderful! (1,003 reviews)

Jan 16 - Jan 19

3 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $377, price is now $232 per person
$232
per person
found 1 day ago
Had a wonderful two nights stay. The staff were all extremely friendly and the room was very comfortable.

Reviewed on Jun 11, 2025

Top rated hotels for your Chicago vacation package

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
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.
Pool
Breakfast included
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
The price is $98 total per night
$98 total
per night
Dec 7 - Dec 8
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.
Pet friendly
Free WiFi
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
The price is $146 total per night
$146 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, access to locker space, and luggage storage. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa
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