Northwest Chicago Vacation Packages

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Top Northwest Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Aug 30 - Sep 5
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
Convenient location for our stay in Chicago. Room could use updating, carpet could use deep cleaning.

Reviewed on Jul. 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Bathroom would be better with 2 bathrooms and one live outlet to enable charging devices while out of the room.

Reviewed on Jul. 30, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on Jul. 30, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on Jul. 30, 2025

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Northwest Chicago Hotel Deals

Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $170 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,181 reviews)
"Staff were nice, beautiful lobby, room was great, and the breakfast was outstanding; would definitely stay again! Also, conveniently close to the mall, plenty of dining options, and the highway. Highly recommend"

Reviewed on Jul. 28, 2025

Hyatt Regency Schaumburg Chicago
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $202 per night from Aug 24 to Aug 25
CA $202
CA $237 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
"It is renovated, it is very clean, the breakfast was delicious"

Reviewed on Jul. 30, 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Aug 22 to Aug 23
CA $248
CA $291 total
Aug 22 - Aug 23
includes taxes & fees
8/10 Very Good! (2,091 reviews)
Very comfortable
"We always stay here before we travel. This time we took advantage of the main restaurant and it was very delightful. The food was fantastic! The best steak and calamari. The atmosphere was a little unexpected especially for our son. Our room was cool and clean and the beds as usual are very ..."

Reviewed on Jul. 29, 2025

Hilton Chicago O'Hare Airport
See all 3,823 properties in Northwest Chicago
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Northwest Chicago

Woodfield Mall featuring shopping as well as a small group of people

Woodfield Mall

Browse through over 300 stores, restaurants and specialty shops at Schaumburg’s expansive shopping mall, one of the largest in the United States.

Woodfield Mall
Legoland Discovery Center featuring art

LEGOLAND® Discovery Center

See iconic Chicago landmarks made from over a million LEGO® pieces, watch a movie and learn how the bricks are made in the LEGO® factory.

LEGOLAND® Discovery Center

NOW Arena

Catch an event at NOW Arena during your trip to Hoffman Estates. Amble around this quaint area's lakeside or attend a sporting event.

NOW Arena

What to do in Northwest Chicago

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Northwest Chicago

Frequently asked questions

How much does a Northwest Chicago vacation package cost?
Much less than you might think — from as low as CA $933, actually! By bundling hotels, flights and car rentals into your own tailor-made vacation package, your Northwest Chicago escape is only clicks away.
How do I get a cheap travel package to Northwest Chicago?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Northwest Chicago vacation package and save. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to tailor your vacation your way. We offer more than 550 airlines and 1,000,000 hotels in all corners of the globe, so that everyone has an opportunity to travel and fulfill those vacation dreams.
What are the top hotels in Northwest Chicago?
When it comes to properties in Schaumburg, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are two popular options. If you're also visiting West Dundee, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my Northwest Chicago vacation?
Reserving your spot early with Expedia means one less thing to worry about. Many air carriers advertise prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, great deals to Northwest Chicago are still known to appear in the weeks leading up to departure.
What does an Expedia Northwest Chicago travel package include?
It depends on what type of escape you have in mind. Northwest Chicago vacation deals can include hotels, flights and car rentals. You can mix and match to create the travel package that suits you. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking a Northwest Chicago travel package?
A travel package can be tailored to your budget and is a fantastic way to stretch your dollars further. What you include is totally up to you. Rental cars, hotels and flights — choose any combination that suits your plans.
Can I choose my airline with a Northwest Chicago Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're in control. We have access to more than 550 airline partners all over the world, so you have loads of choice when arranging your Northwest Chicago adventure.
If I'm not able to travel, can I cancel my Northwest Chicago vacation package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Northwest Chicago vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.