Northwest Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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 illuminated buildings, a river, and a bridge.

Irving Park

5 out of top 10 points of interest in this area

Irving Park is well liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Avondale Music Hall are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

Find hotels in Irving Park
A city skyline with modern skyscrapers, a river, and a marina.

Dunning

Restaurants and parks are just a few things travellers like about Dunning. A stop by Schiller Woods is also recommended if you've got time to explore the area.

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

Portage Park

3 out of top 10 points of interest in this area

If you're spending some time in Portage Park, Milwaukee Avenue and Six Corners are top sights worth seeing.

Find hotels in Portage Park
A panoramic view of a city skyline with prominent skyscrapers, a river, and a bridge.

Belmont Cragin

1 out of top 10 points of interest in this area

Belmont Cragin is well liked for its restaurants and live music. If you're hoping to see more of the larger area, Walt Disney House and Frank Lloyd Wright Historic District are some interesting sights nearby to check out.

Find hotels in Belmont Cragin
The Chicago Theatre with a prominent marquee displaying movie titles.

Hermosa

1 out of top 10 points of interest in this area

Travellers like the historical sites in Hermosa, and Walt Disney House is a top attraction you might want to visit.

Find hotels in Hermosa

Top hotels in Northwest Side

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
4.516.211 ₫
5.369.324 ₫ total
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,205 reviews)
"My stay was great. But the hallway was off putting."

Reviewed on 10 Sept 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
4.638.544 ₫
5.514.767 ₫ total
12 Oct - 13 Oct
includes taxes & fees
8/10 Very good! (2,211 reviews)
"Great location and room!"

Reviewed on 11 Sept 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
4.333.490 ₫
5.152.087 ₫ total
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,426 reviews)
"This hotel was right across the street from the Riverwalk. I loved that amenity. The staff was friendly and helpful."

Reviewed on 11 Sept 2026

River Hotel
See all 4,896 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

Walt Disney House

Learn about the local history of Chicago with a stop at Walt Disney House. Experience the entertainment choices and acclaimed art galleries in this vibrant area.
See properties

Six Corners

You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
See properties

Avondale Music Hall

You can make plans for a show at Avondale Music Hall on your trip to Chicago. Take in the live music while you're in the area.
See properties

Irish American Heritage Center

You can spend an afternoon exploring the galleries in Irish American Heritage Center in Chicago. Take in the live music while you're in the area.
See properties

Hanson Park

After visiting Hanson 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

Live Wire Lounge

After visiting Live Wire Lounge, make a plan to see the other sights and activities in Chicago. Take in the live music while you're in the area.
See properties

COLOR CLUB

COLOR CLUB is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.
See properties

Frequently asked questions

How much does a Northwest Side holiday 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 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 1null000null000 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.

Explore a world of travel with Expedia