Northwest Chicago Vacation Packages

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Top Northwest Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The hotel is situated in Fulton market and has many options for dining. The bed was comfortable, but the linens were very wrinkled and the comforter had stains on it.

Reviewed on Aug. 15, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Food options need more variety.

Reviewed on Aug. 16, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything. We stayed at Fultom before and the River North is really good as well. Only difference slighty better views with sky terrace at Fulton and from pool side and indoor spa. Riverside has game room which my kid and I enjoyed tons of chess. Great place hard to pick one both has pros and really no cons. Look forward to our next stay. Higher floor the better witb views from the room. Great staff as well!

Reviewed on Aug. 15, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 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 $164 per night from Aug 17 to Aug 18
CA $164
CA $189 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,204 reviews)
"Rooms were clean however the bathroom was a little tight for a small family of 3. You can tell they renovated recently which is a plus. Would stay here again if needed to."

Reviewed on Aug. 11, 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 $184 per night from Aug 24 to Aug 25
CA $184
CA $216 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,366 reviews)
"My only issue was my room was right next to the elevator and I can hear it running throughout the day when I was trying to take a nap"

Reviewed on Aug. 12, 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 Sep 5 to Sep 6
CA $248
CA $291 total
Sep 5 - Sep 6
includes taxes & fees
8/10 Very Good! (2,100 reviews)
"Very convenient for early/late flights, room clean, overall quiet, bed was pretty soft/low to the ground, service a little slow."

Reviewed on Aug. 12, 2025

Hilton Chicago O'Hare Airport
See all 3,743 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 $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 $862, 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.