Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Zion by IHG
Save 100% on your flight
Price was $746, price is now $510 per person
$510
per person
Jun 3 - Jun 9
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Carmel Park and Ophir Park are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,124, price is now $674 per person
$674
per person
Jun 18 - Jun 22
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,195, price is now $760 per person
$760
per person
Jun 18 - Jun 22
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 $1,434, price is now $929 per person
$929
per person
Jun 18 - Jun 22
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 $1,500, price is now $979 per person
$979
per person
Jun 18 - Jun 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, 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,067, price is now $698 per person
$698
per person
Jun 18 - Jun 22
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.
The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $1,588, price is now $1,081 per person
$1,081
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Fiserv Forum and Henry W. Maier Festival Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,006, price is now $1,367 per person
$1,367
per person
Jun 18 - Jun 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, a full-service spa, and breakfast (surcharge). 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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
Sonesta Simply Suites Chicago Waukegan
1151 S Waukegan Rd Waukegan IL
Book a stay at this golf hotel in Waukegan. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
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.
Thu, May 7 - Sun, May 10
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$91 Roundtrip, found 12 hours ago
$91
Roundtrip
found 12 hours ago
Mon, May 18 - Thu, May 28
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$160 Roundtrip, just found
$160
Roundtrip
just found
Sat, May 23 - Fri, May 29
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Sun, May 10 - Fri, May 15
DEN
Denver Intl.
MKE
General Mitchell Intl.
$164 Roundtrip, found 4 days ago
$164
Roundtrip
found 4 days ago
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