Northwest Side Vacation Packages

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Top Northwest Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (1,003 reviews)
Nice hotel in a nice area

Reviewed on Aug. 5, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 24 - Oct 27
found 1 day 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

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,048 reviews)
Our family loves to stay at the Hilton. It's close to many classic Chicago sites. You have a wonderful deep dish pizza around the corner. The staff are always friendly and efficient.

Reviewed on Aug. 15, 2025

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

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,067 reviews)
The room was spacious, clean, and updated. The area was perfect to get anywhere we wanted. The staff was kind and helpful. The rooftop pool was very nice.

Reviewed on Aug. 15, 2025

Where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.

Find hotels in Irving Park

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Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,916 reviews)
"Great views of the lake. Good location for museum campus and northerly island."

Reviewed on Aug. 14, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Sep 3 to Sep 4
CA $222
CA $261 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,703 reviews)
"T"

Reviewed on Aug. 15, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Sep 2 to Sep 3
CA $240
CA $316 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,853 reviews)
"Great hotel. The lobby is a must-see!"

Reviewed on Aug. 13, 2025

Palmer House a Hilton Hotel
See all 4,978 properties in Northwest Side
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 Side

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Northwest Side

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 Side

Frequently asked questions

How much does a Northwest Side vacation package cost?
Explore the best of Northwest Side from just CA $632. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Northwest Side?
Book everything all in one place with our Northwest Side vacation packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you'll have the flexibility to mix and match as you like.
How far in advance should I book my Northwest Side vacation?
Savvy travelers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Northwest Side travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're headed to Northwest Side on a family road trip or traveling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on some activities?
Can I choose my airline with a Northwest Side Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Northwest Side vacation package?
Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.