Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,134, price is now $674 per person
$674
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,540, price is now $881 per person
$881
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,512, price is now $886 per person
$886
per person
Jul 22 - Jul 26
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 Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,335, price is now $824 per person
$824
per person
Jul 22 - Jul 26
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 $1,546, price is now $997 per person
$997
per person
Jul 22 - Jul 26
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.
L7 Chicago by LOTTE
Downtown Chicago
Save 100% on your flight
Price was $1,908, price is now $1,231 per person
$1,231
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,487, price is now $968 per person
$968
per person
Jul 22 - Jul 26
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 Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,580, price is now $1,040 per person
$1,040
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 ...
Wyndham Garden Kenosha Harborside
5125 6th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
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 ...
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.
Mon, Sep 14 - Mon, Sep 21
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$144 Roundtrip, found 6 days ago
$144
Roundtrip
found 6 days ago
Sat, Aug 15 - Tue, Sep 1
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Mon, Aug 10 - Tue, Aug 25
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$228 Roundtrip, found 17 hours ago
$228
Roundtrip
found 17 hours ago
Fri, Jul 3 - Sat, Jul 4
TPA
Tampa Intl.
MKE
General Mitchell Intl.
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
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