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Uptown Vacation Packages

Uptown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $1,144, price is now $792 per person
$792
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ryan Field and Baha'i House of Worship are located nearby.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $2,348, price is now $1,671 per person
$1,671
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.
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,916, price is now $1,403 per person
$1,403
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 American Family Field and Fiserv Forum are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
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

The Emily Hotel

4 out of 5
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 14 hours 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
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 8 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,264, price is now $835 per person
$835
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.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,744, price is now $1,834 per person
$1,834
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 breakfast (surcharge). Our guests praise the helpful staff 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.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $1,144, price is now $792 per person
$792
per person
Oct 21 - Oct 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 $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)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,907, price is now $1,301 per person
$1,301
per person
Oct 2 - Oct 6
found 12 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
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 12 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)

5-7 Night Vacations in Uptown

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,832, price is now $983 per person
$983
per person
Oct 15 - Oct 20
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $2,348, price is now $1,671 per person
$1,671
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
The Emily Hotel

The Emily Hotel

4 out of 5
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 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,459, price is now $1,582 per person
$1,582
per person
Oct 15 - Oct 20
found 14 hours 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
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
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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
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 Gurnee Mills are located ...
Opens in a new windowDays Inn by Wyndham Waukegan
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
Hampton Inn Chicago - Gurnee

Hampton Inn Chicago - Gurnee

2.5 out of 5
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 ...
Opens in a new windowHampton Inn Chicago - 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
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.

Bargain Flight
Wed, Nov 18 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$229 Roundtrip, found 6 hours ago
$229
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Wed, Nov 18 from Hartsfield-Jackson Atlanta Intl. to General Mitchell Intl., returning Wed, Dec 2, priced at $229 found 6 hours ago
Bargain Flight
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
Select Bargain Flight flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Wed, Oct 28, priced at $240 found 2 days ago
Bargain Flight
Fri, Sep 11 - Sat, Sep 12
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$249 Roundtrip, found 8 hours ago
$249
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Fri, Sep 11 from Philadelphia Intl. to General Mitchell Intl., returning Sat, Sep 12, priced at $249 found 8 hours ago
Sun Country Airlines
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
Select Sun Country Airlines flight, departing Wed, Nov 25 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Nov 29, priced at $257 found 2 days ago