Northwest Side Vacations

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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
A city skyline with several high-rise buildings, including a prominent glass skyscraper and a building with a spire.

Portage Park

5 out of top 10 points of interest in this area

While visiting Portage Park, you might make a stop by sights like Milwaukee Avenue and Six Corners.

Find hotels in Portage Park

Find the Best Northwest Side Vacation Packages

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 NT$3,817 per night from Nov 22 to Nov 23
NT$3,817
NT$4,538 total
Nov 22 - Nov 23
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$3,813 per night from Dec 1 to Dec 2
NT$3,813
NT$4,533 total
Dec 1 - Dec 2
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$3,255 per night from Dec 15 to Dec 16
NT$3,255
NT$3,870 total
Dec 15 - Dec 16
includes taxes & fees
8.8/10 Excellent! (5,617 reviews)
"Amazing spot right in the middle of the action, shopping to the north and attractions to the south. The river right beside the hotel and the lake a short walk away. My room was a little tight but I am not in Chicago to be in my room. Would stay here again in a heartbeat."

Reviewed on 2026/11/14

River Hotel
See all 4,877 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.

Stay near popular Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
See properties

Frequently asked questions

How much does a Northwest Side vacation package cost?
Explore the best of Northwest Side from just . 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.