Search Deals on
Chicago Premium Outlets Vacation Packages

Chicago Premium Outlets Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $548, price is now $386 per person
$386
per person
Mar 18 - Mar 23
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 room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $822, price is now $453 per person
$453
per person
Mar 18 - Mar 23
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $480 per person
$480
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $801, price is now $513 per person
$513
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $769, price is now $501 per person
$501
per person
Mar 18 - Mar 23
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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,818, price is now $1,205 per person
$1,205
per person
Mar 22 - Mar 27
found 24 hours 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,269, price is now $855 per person
$855
per person
Mar 13 - Mar 17
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,026, price is now $693 per person
$693
per person
Mar 12 - Mar 17
found 14 hours 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. 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 $1,009, price is now $682 per person
$682
per person
Mar 4 - Mar 11
found 11 hours 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.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $625, price is now $432 per person
$432
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field 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
Save 100% on your flight
Price was $773, price is now $538 per person
$538
per person
Mar 18 - Mar 23
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.
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Save 100% on your flight
Price was $594, price is now $416 per person
$416
per person
Mar 18 - Mar 23
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 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.

3-4 Night Vacations in Chicago Premium Outlets

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 $531, price is now $315 per person
$315
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $480 per person
$480
per person
Mar 12 - Mar 16
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 $958, price is now $648 per person
$648
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $441 per person
$441
per person
Mar 11 - Mar 14
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $453 per person
$453
per person
Mar 18 - Mar 23
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
Save 100% on your flight
Price was $801, price is now $513 per person
$513
per person
Mar 18 - Mar 23
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 $769, price is now $501 per person
$501
per person
Mar 18 - Mar 23
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 $1,488, price is now $971 per person
$971
per person
Mar 2 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Chicago Premium Outlets Last Minute Hotel Deals

Motel 6 Naperville, IL

Motel 6 Naperville, IL

2 out of 5
1585 Naperville Wheaton Road Naperville IL
Stay at this motel in Naperville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Motel 6 Naperville, IL
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
1823 Abriter Court 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 ...
Embassy Suites by Hilton Chicago Naperville
Hampton Inn Chicago/Naperville

Hampton Inn Chicago/Naperville

2.5 out of 5
1087 E Diehl 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 helpful staff in our reviews. ...
Hampton Inn Chicago/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
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
2111 Butterfield Rd Downers Grove IL
Book a stay at this golf hotel in Downers Grove. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our ...
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
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
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 onsite spa services. Popular attractions Ty Warner Park and Yorktown Shopping Center ...
Sybaris Pool Suites
Homewood Suites By Hilton Downers Grove Chicago, Il

Homewood Suites By Hilton Downers Grove Chicago, Il

3 out of 5
1500A Opus Place Downers Grove IL
Book a stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Homewood Suites By Hilton Downers Grove Chicago, Il
See all 2,345 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.