Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $811, price is now $514 per person
$514
per person
Jun 30 - Jul 4
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 Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $613 per person
$613
per person
Jul 2 - Jul 8
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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,384, price is now $789 per person
$789
per person
Jul 2 - Jul 8
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 $1,377, price is now $835 per person
$835
per person
Jul 2 - Jul 8
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.
La Banque Hotel
Save 100% on your flight
Price was $1,104, price is now $687 per person
$687
per person
Jul 2 - Jul 7
found 21 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,024, price is now $655 per person
$655
per person
Jul 2 - Jul 8
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 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $884, price is now $570 per person
$570
per person
Jul 2 - Jul 8
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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,129, price is now $731 per person
$731
per person
Jul 2 - Jul 8
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.
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 ...
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 ...
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, Sep 1 - Thu, Sep 3
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Wed, Aug 12 - Tue, Aug 25
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Wed, Jul 22 - Sat, Jul 25
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Wed, May 27 - Wed, Jun 3
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
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