Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
9.2/10 Wonderful! (1,006 reviews)
Mar 19 - Mar 22
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $448, price is now $299 per person
$299
per person
found 1 day ago
Great location and friendly staff.
Reviewed on May 14, 2025
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
9.2/10 Wonderful! (317 reviews)
Mar 19 - Mar 22
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $618, price is now $369 per person
$369
per person
found 1 day ago
close to everything we will be staying here again on our next vacation to Chicago
Reviewed on Aug 31, 2024
4.5-star property
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
9/10 Wonderful! (1,002 reviews)
Mar 20 - Mar 25
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $758, price is now $476 per person
$476
per person
found 1 day ago
The location couldn’t be better—right across from The Bean. The hotel is gorgeous, old-style elegance with a beautiful, antique-like bar, a cozy fireplace, and fabulous wooden details throughout. The food and drinks were excellent.
The service was outstanding and attentive, from the bellman to the janitorial staff. The rooms are spacious, with a very comfortable large king bed. Overall, a great experience. I highly recommend it!
Reviewed on Dec 24, 2025
2.0-star property
4BR Corporate Suite Central and Modern
Near North Side
10/10 Exceptional! (8 reviews)
Mar 13 - Mar 16
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,152, price is now $1,398 per person
$1,398
per person
found 4 hours ago
5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
9.4/10 Exceptional! (1,000 reviews)
Mar 16 - Mar 18
2 night stay
Dallas (DFW) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $810, price is now $540 per person
$540
per person
found 2 hours ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!
Reviewed on Dec 31, 2025
Top rated hotels for your Chicago vacation package
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.6 mi from city center
The price is $192 total per night
$192 total
per night
Jan 11 - Jan 12
Guests staying at Hilton Chicago enjoy an indoor pool, a gym, and a sauna. Valet parking is offered for USD 88.00 per day. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include free WiFi in public areas, a hot tub, and a conference 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 $105 total per night
$105 total
per night
Jan 7 - Jan 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.
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 $192 total per night
$192 total
per night
Jan 7 - Jan 8
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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