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Uptown Vacation Packages

Uptown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $315 per person
$315
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,061, price is now $601 per person
$601
per person
Dec 24 - Dec 29
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
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.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,108, price is now $704 per person
$704
per person
Dec 16 - Dec 23
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $735, price is now $469 per person
$469
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,025, price is now $660 per person
$660
per person
Dec 24 - Dec 29
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $527 per person
$527
per person
Dec 24 - Dec 29
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $733, price is now $502 per person
$502
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.

3-4 Night Vacations in Uptown

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

4 out of 5
Price was $526, price is now $353 per person
$353
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,482, price is now $470 per person
$470
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $599, price is now $400 per person
$400
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $601, price is now $411 per person
$411
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Uptown

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $315 per person
$315
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,663, price is now $675 per person
$675
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,061, price is now $601 per person
$601
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in Uptown

La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
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 ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Chicago Gurnee
The Inn on Sheridan

The Inn on Sheridan

3.5 out of 5
2723 Sheridan Rd Zion IL
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Inn on Sheridan
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
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. ...
Opens in a new windowGreat Wolf Lodge Illinois
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Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
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 ...
Opens in a new windowSonesta ES Suites Chicago Waukegan Gurnee
Americas Best Value Inn & Suites Racine

Americas Best Value Inn & Suites Racine

2 out of 5
5419 Durand Ave Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in ...
Opens in a new windowAmericas Best Value Inn & Suites Racine
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

2 out of 5
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 ...
Opens in a new windowDays Inn by Wyndham Sturtevant / Racine / Mount Pleasant
Courtyard Chicago Waukegan Gurnee

Courtyard Chicago Waukegan Gurnee

3 out of 5
3800 Northpoint Blvd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Opens in a new windowCourtyard Chicago Waukegan Gurnee
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

2.5 out of 5
7011 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 helpful staff and the clean ...
Opens in a new windowCountry Inn & Suites by Radisson Kenosha - Pleasant Prairie
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.

Frontier Airlines
Tue, Nov 24 - Mon, Dec 7
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$123 Roundtrip, found 7 hours ago
$123
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Orlando Intl. to General Mitchell Intl., returning Mon, Dec 7, priced at $123 found 7 hours ago
Bargain Flight
Thu, Nov 12 - Sun, Nov 22
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$206 Roundtrip, just found
$206
Roundtrip
just found
Select Bargain Flight flight, departing Thu, Nov 12 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Nov 22, priced at $206 just found
Sun Country Airlines
Thu, Dec 17 - Thu, Dec 24
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$208 Roundtrip, found 10 hours ago
$208
Roundtrip
found 10 hours ago
Select Sun Country Airlines flight, departing Thu, Dec 17 from Sky Harbor Intl. to General Mitchell Intl., returning Thu, Dec 24, priced at $208 found 10 hours ago
Frontier Airlines
Fri, Dec 25 - Thu, Jan 14
DEN
Denver Intl.
MKE
General Mitchell Intl.
$228 Roundtrip, found 3 hours ago
$228
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Dec 25 from Denver Intl. to General Mitchell Intl., returning Thu, Jan 14, priced at $228 found 3 hours ago