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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.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star 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.
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Pirates Cove Childrens Theme Park are located nearby.
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, 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 Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy a sauna, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Grant Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and the bar in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Jaslin Hotel

Jaslin Hotel

3 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 4-star 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.
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3 out of 5
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
per person
May 20 - May 25
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.

3-4 Night Vacations in Chicago Premium Outlets

Price found within the past 48 hours. Click for updated prices.
Alpine Inn Rockford

Alpine Inn Rockford

2.5 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Days Inn by Wyndham Rockford I-90 Casino District

Days Inn by Wyndham Rockford I-90 Casino District

2.5 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Super 8 by Wyndham Rochelle

Super 8 by Wyndham Rochelle

2 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockford (RFD)
Super 8 by Wyndham DeKalb IL

Super 8 by Wyndham DeKalb IL

2 out of 5
per person
May 23 - May 26
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.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
O'Hare
Save 100% on your flight
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 10 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 20 - May 25
found 10 hours ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)

Chicago Premium Outlets Last Minute Hotel Deals

Best Western Naperville Inn
Best Western Naperville Inn
2.5 out of 5
1617 Naperville Wheaton Rd, Naperville, IL
Book a stay at this eco-certified hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Naperville Inn
DoubleTree by Hilton Lisle Naperville
DoubleTree by Hilton Lisle Naperville
4 out of 5
3003 Corporate West Dr, Naperville, IL
Stay at this 4-star 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
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
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
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
Stay at this 3-star 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
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
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
The Westin Chicago Lombard
The Westin Chicago Lombard
4 out of 5
70 Yorktown Center, Lombard, IL
Stay at this 4-star 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 2,034 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.