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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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $879, price is now $629 per person
$629
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and 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 $2,135, price is now $1,225 per person
$1,225
per person
Sep 28 - Oct 5
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,633, price is now $981 per person
$981
per person
Sep 23 - Sep 27
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.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $4,897, price is now $2,949 per person
$2,949
per person
Sep 13 - Sep 19
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,408, price is now $881 per person
$881
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,934, price is now $1,258 per person
$1,258
per person
Sep 17 - Sep 22
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.
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 $1,531, price is now $1,015 per person
$1,015
per person
Sep 23 - Sep 27
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,683, price is now $1,140 per person
$1,140
per person
Sep 17 - Sep 22
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,390, price is now $970 per person
$970
per person
Sep 17 - Sep 22
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.
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $2,101, price is now $1,473 per person
$1,473
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field 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 $1,679, price is now $1,215 per person
$1,215
per person
Sep 17 - Sep 22
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. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,594, price is now $1,154 per person
$1,154
per person
Sep 28 - Oct 5
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 breakfast and the pool 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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $627, price is now $376 per person
$376
per person
Oct 3 - Oct 6
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 $1,076, price is now $653 per person
$653
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $861, price is now $524 per person
$524
per person
Oct 3 - Oct 6
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 $1,082, price is now $702 per person
$702
per person
Sep 25 - Sep 28
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 $1,866, price is now $1,106 per person
$1,106
per person
Sep 19 - Sep 24
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 $2,135, price is now $1,225 per person
$1,225
per person
Sep 28 - Oct 5
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 $2,792, price is now $1,664 per person
$1,664
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $4,897, price is now $2,949 per person
$2,949
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
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
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
Best Western Chicago - Downers Grove

Best Western Chicago - Downers Grove

2.5 out of 5
3010 Finley Rd 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 breakfast and the helpful ...
Best Western Chicago - 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
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
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 Oakbrook Center Mall and Ty Warner Park are ...
Sybaris Pool Suites
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
70 Yorktown Center Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
The Westin Chicago Lombard
See all 2,286 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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