Search Deals on
Chicago Premium Outlets Vacation Packages

Chicago Premium Outlets Flight + Hotel Packages

The Langham, Chicago

The Langham, Chicago

5 out of 5
Price was $1,785, price is now $1,126 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the property condition in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $729, price is now $508 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the bar in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for LondonHouse Chicago, Curio Collection by Hilton, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $727, price is now $539 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, 3 bars/lounges, and a rooftop terrace. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Chicago Athletic Association, a Hyatt Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was $1,555, price is now $1,174 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Waldorf Astoria Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop

4 out of 5
Price was $703, price is now $547 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the comfy rooms and the overall value in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Canopy by Hilton Chicago Central Loop, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $1,400, price is now $1,093 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Park Hyatt Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Price was $756, price is now $599 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy a full-service spa, breakfast, and WiFi. Our guests praise the property condition in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Palmer House a Hilton Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Price was $1,885, price is now $1,501 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The Peninsula Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pendry Chicago

Pendry Chicago

5 out of 5
Price was $831, price is now $668 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the property condition in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Pendry Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Price was $737, price is now $597 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast, WiFi, and room service. Popular attractions Navy Pier and Millennium Park are located nearby. Discover genuine guest reviews for W Chicago - Lakeshore, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Price was $1,067, price is now $893 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the bar in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Hyatt Regency Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $599, price is now $506 per person
per person
Nov 15 - Nov 19
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Kinzie Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

3-4 Night Vacations in Chicago Premium Outlets

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flightPrice was $595, price is now $435 per person
per person
Oct 26 - Oct 29
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flightPrice was $878, price is now $643 per person
per person
Nov 10 - Nov 13
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flightPrice was $815, price is now $614 per person
per person
Oct 30 - Nov 2
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
Downtown Chicago
Price was $489, price is now $373 per person
per person
Oct 26 - Oct 29
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Prices and availability subject to change. Additional terms may apply.

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. Popular attractions Naperville Yard Indoor Sports Complex and Nike ...
Motel 6 Naperville, IL
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. Popular attractions Naperville Yard Indoor Sports Complex ...
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
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free parking, and WiFi. Our guests praise the property condition in our reviews. Popular ...
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
Stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. ...
Best Western Chicago - Downers Grove
Crowne Plaza Lombard Downers Grove, an IHG Hotel
Crowne Plaza Lombard Downers Grove, an IHG Hotel
3.5 out of 5
1250 Roosevelt Road, Glen Ellyn, IL
Stay at this 3.5-star business-friendly hotel in Glen Ellyn. Enjoy free WiFi, free parking, and breakfast. Popular attractions Lilacia Park and Yorktown Shopping ...
Crowne Plaza Lombard Downers Grove, an IHG Hotel
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 free parking, 2 restaurants, and breakfast. Our guests praise the property condition in our reviews. ...
The Westin Chicago Lombard
Fairfield Inn & Suites by Marriott Lombard
Fairfield Inn & Suites by Marriott Lombard
2.5 out of 5
645 W North Ave, Lombard, IL
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. ...
Fairfield Inn & Suites by Marriott 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
Stay at this 3.5-star business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the property condition ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 1,881 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.

Book the perfect getaway to Chicago Premium Outlets

With Hotwire, booking your next trip to Aurora is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Chicago Premium Outlets while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Chicago Premium Outlets flight and hotel package for as low as $373.

Living it up in Aurora means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Chicago Premium Outlets, Aurora vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Chicago Premium Outlets for some of the best accommodations and flight deals.

FAQs about cheap Chicago Premium Outlets packages:

How to get cheap vacation deals to Chicago Premium Outlets?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $51.

How much are Chicago Premium Outlets packages?

Vacation packages to Chicago Premium Outlets vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $373.

How to find cheap car rentals near Chicago Premium Outlets?

Hotwire partners with some of the most reliable car rental companies in Aurora to bring you the best car rental deals in Chicago Premium Outlets for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Chicago Premium Outlets now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chicago Premium Outlets right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Discover Other Travel Deals