Downtown Chicago flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
W Chicago - Lakeshore
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
Top Downtown Chicago hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
Jul 1 - Jul 2
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $182 per night
$182
per night
Jul 2 - Jul 3
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
Jun 30 - Jul 1
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $170 per night
$170
per night
Jul 10 - Jul 11
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
Jun 30 - Jul 1
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
Jul 2 - Jul 3
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.
Air conditioning
Gym
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View all propertiesLowest 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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