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Uptown Vacation Packages

3-4 Night Vacations in Uptown

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $800, price is now $506 per person
$506
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,350, price is now $901 per person
$901
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 $954, price is now $695 per person
$695
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,008, price is now $737 per person
$737
per person
May 22 - May 25
found 11 hours 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.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Save 100% on your flight
Price was $551, price is now $354 per person
$354
per person
May 17 - May 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was $1,216, price is now $887 per person
$887
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,271, price is now $934 per person
$934
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $997, price is now $634 per person
$634
per person
May 9 - May 14
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Cheap Hotel Deals in Uptown

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
Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

2.5 out of 5
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 ...
Opens in a new windowBest Western Executive Inn Kenosha/Pleasant Prairie
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
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Days Inn by Wyndham Waukegan

Days Inn by Wyndham Waukegan

2 out of 5
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 The People's Choice Family ...
Opens in a new windowDays Inn by Wyndham Waukegan
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
Comfort Suites Grayslake near Libertyville North

Comfort Suites Grayslake near Libertyville North

2.5 out of 5
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 ...
Opens in a new windowComfort Suites Grayslake near Libertyville North
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
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
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 ...
Opens in a new windowThe Stella Hotel & Ballroom
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, May 5 - Fri, May 8
DEN
Denver Intl.
MKE
General Mitchell Intl.
$140 Roundtrip, found 15 hours ago
$140
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Denver Intl. to General Mitchell Intl., returning Fri, May 8, priced at $140 found 15 hours ago
Frontier Airlines
Thu, May 7 - Sun, May 17
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$144 Roundtrip, found 4 hours ago
$144
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, May 7 from Orlando Intl. to General Mitchell Intl., returning Sun, May 17, priced at $144 found 4 hours ago
Frontier Airlines
Thu, Apr 23 - Wed, May 6
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Sky Harbor Intl. to General Mitchell Intl., returning Wed, May 6, priced at $180 found 7 hours ago
Frontier Airlines
Sat, Apr 18 - Mon, Apr 27
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Hartsfield-Jackson Atlanta Intl. to General Mitchell Intl., returning Mon, Apr 27, priced at $194 found 5 days ago