Northwest Side Packages (Flight + Hotel)

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Top Northwest Side Flight + Hotel Deals

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 9 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
There was an odd odor. My room was not ready for several hours after check in.

Reviewed on 17 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
I had a great stay. No complaints. The staff was great.

Reviewed on 17 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 9 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The room is spacious and the bedding is comfortable. The washroom is sparkling clean. The breakfast buffet is an excellent addition to our stay. We all love it.

Reviewed on 18 Jul 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

Top hotels in Northwest Side

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 ฿5,759 per night from 4 Aug to 5 Aug
฿5,759
฿6,761 total
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,856 reviews)
"I loved everything about my stay at the congress plaza. Were the rooms updated no. But it had it charm. I am in love with the designs of the 1920. The staff were extremely accommodating. They did not even charge me for late check out. I will be staying here again."

Reviewed on 16 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ฿8,961 per night from 10 Aug to 11 Aug
฿8,961
฿11,558 total
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"Very close to popular places."

Reviewed on 16 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,667 per night from 17 Aug to 18 Aug
฿4,667
฿5,478 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,454 reviews)
Connecting room
"Hotel property was amazing. Room was very clean and staff was friendly. Location was perfect. I was shocked to find that my room was connected to another room by just a deadbolt and door jam. That made me feel very uncomfortable and could barely sleep. By the time I realized that, I felt that it ..."

Reviewed on 16 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,947 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

฿1,592
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

฿1,469
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

฿1,469
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Northwest Side

Frequently asked questions

How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just ฿13,736. 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 holiday 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 holiday?
Savvy travellers 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 travelling 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 holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday 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 holiday 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.