Deals on vacations and trips to Uptown
Uptown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area, luggage storage, and concierge services are also on offer.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Top Uptown hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Jun 29 - Jun 30
Total includes taxes and fees
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
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $184 total per night
$184 total
Jun 29 - Jun 30
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
$161 nightly
The price is $189 total per night
$189 total
Jun 29 - Jun 30
Total includes taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $198 total per night
$198 total
Jun 30 - Jul 1
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago, IL
$231 nightly
The price is $271 total per night
$271 total
Jun 29 - Jun 30
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Spa
Pet friendly
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$167 nightly
The price is $196 total per night
$196 total
Jun 3 - Jun 4
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.
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.
Popular places to visit
Lincoln Park
This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.
Montrose Beach
If a restful vacation is part of your travel plans, Montrose Beach might be the perfect place to seek out during your trip to Chicago. Stroll along the lakeside or discover the area's sunrises.
Montrose Harbor
Explore the waterfront in Chicago with a trip to Montrose Harbor. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
Frequently asked questions
Photos of local treasures
Browse Uptown vacation photos for more inspiration
