Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,276, price is now $750 per person
$750
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Wade
Downtown Chicago
Save 100% on your flight
Price was $1,754, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,259, price is now $755 per person
$755
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,936, price is now $1,198 per person
$1,198
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,242, price is now $776 per person
$776
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,681, price is now $1,073 per person
$1,073
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,505, price is now $981 per person
$981
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $2,012, price is now $1,319 per person
$1,319
per person
Jul 1 - Jul 5
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee Art Museum and Fiserv Forum are located nearby.
3-4 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Uptown
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Stay at this motel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Six Flags Great America and Gurnee Mills are located ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Save an average of 15% on thousands of hotels when you're signed in
Wingate by Wyndham Gurnee
6090 Gurnee Mills Blvd E Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Days Inn by Wyndham Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
Book a stay at this family-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
Book a stay at this business-friendly hotel in Grayslake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Aug 4 - Tue, Aug 18
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$151 Roundtrip, found 20 hours ago
$151
Roundtrip
found 20 hours ago
Wed, Aug 12 - Tue, Aug 25
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$190 Roundtrip, found 23 hours ago
$190
Roundtrip
found 23 hours ago
Wed, Jun 3 - Tue, Jun 9
TTN
Mercer
MKE
General Mitchell Intl.
$195 Roundtrip, found 15 hours ago
$195
Roundtrip
found 15 hours ago
Wed, Jun 17 - Tue, Jun 30
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
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