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Chicago Premium Outlets Vacation Packages

Chicago Premium Outlets Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Save 100% on your flight
Price was $403, price is now $292 per person
$292
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free parking, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Topgolf are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $574, price is now $392 per person
$392
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $985, price is now $681 per person
$681
per person
Nov 21 - Nov 25
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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $479, price is now $334 per person
$334
per person
Dec 7 - Dec 11
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $683, price is now $479 per person
$479
per person
Nov 23 - Nov 28
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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $973, price is now $706 per person
$706
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $972, price is now $708 per person
$708
per person
Nov 23 - Nov 28
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,831, price is now $1,340 per person
$1,340
per person
Dec 3 - Dec 7
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.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Save 100% on your flight
Price was $474, price is now $351 per person
$351
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $607, price is now $451 per person
$451
per person
Nov 12 - Nov 16
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 Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Chicago Premium Outlets

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $562, price is now $373 per person
$373
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $742, price is now $497 per person
$497
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Greater Grand Crossing
Save 100% on your flight
Price was $677, price is now $460 per person
$460
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Chicago Premium Outlets

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 $694, price is now $459 per person
$459
per person
Nov 23 - Nov 28
found 1 day 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 $2,059, price is now $1,190 per person
$1,190
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Chicago Premium Outlets Last Minute Hotel Deals

Hollywood Casino Aurora

Hollywood Casino Aurora

2 out of 5
2500 N Farnsworth Ave Aurora IL
Book a stay at this spa hotel in Aurora. Enjoy a full-service spa, 9 restaurants, and a 24-hour fitness center. Popular attractions Chicago Premium Outlets and ...
Hollywood Casino Aurora
Hotel Arista

Hotel Arista

4.5 out of 5
2139 City Gate Ln Naperville IL
Book a stay at this luxury hotel in Naperville. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hotel Arista
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Lisle Naperville
Best Western Naperville Inn

Best Western Naperville Inn

2.5 out of 5
1617 Naperville Wheaton Rd Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Naperville Inn
Studio 6 Corporate Extended Stay Chicago Lisle IL

Studio 6 Corporate Extended Stay Chicago Lisle IL

3 out of 5
445 Warrenville Rd Lisle IL
Stay at this hotel in Lisle. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Oakbrook Center Mall and Belmont Prairie Nature Preserve ...
Studio 6 Corporate Extended Stay Chicago Lisle IL
Sybaris Pool Suites

Sybaris Pool Suites

2.5 out of 5
600 Ogden Ave Downers Grove IL
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
Sybaris Pool Suites
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
SureStay Plus Hotel by Best Western Chicago Lombard
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 2,326 properties in Chicago Premium Outlets
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.

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