Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,242, price is now $822 per person
$822
per person
Oct 21 - Oct 25
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.
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was $2,358, price is now $1,677 per person
$1,677
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,561, price is now $877 per person
$877
per person
Oct 11 - Oct 15
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $2,168, price is now $1,224 per person
$1,224
per person
Oct 15 - Oct 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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,761, price is now $1,712 per person
$1,712
per person
Oct 11 - Oct 15
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $926 per person
$926
per person
Oct 3 - Oct 7
found 20 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
L7 Chicago by LOTTE
Downtown Chicago
Save 100% on your flight
Price was $1,351, price is now $960 per person
$960
per person
Oct 11 - Oct 15
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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,584, price is now $1,130 per person
$1,130
per person
Oct 2 - Oct 6
found 23 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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.
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
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 ...
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. ...
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 parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
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 ...
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave 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 ...
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.
Wed, Nov 18 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$229 Roundtrip, found 18 hours ago
$229
Roundtrip
found 18 hours ago
Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Fri, Sep 11 - Sat, Sep 12
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$249 Roundtrip, found 20 hours ago
$249
Roundtrip
found 20 hours ago
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
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