Northwest Side Holidays

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Our guide on 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

4 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.

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

Portage Park

4 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.

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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.

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JS999940

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.

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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.

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Northwest Side Holiday

Our pick of the best Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$208
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,237 reviews)
"Room was clean, bathroom was old and a bit smelly. Was fine for the one night we were there - a bit pricey tho"

Reviewed on 31 Aug 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
NZ$287
1 Sept - 2 Sept
includes taxes & fees
8/10 Very good! (2,133 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"

Reviewed on 31 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
9.4/10 Exceptional! (882 reviews)
"Love the layout. Great location. Super easy check in and check out"

Reviewed on 30 Aug 2026

Get rates
Kasa Magnificent Mile Chicago
See all 4,884 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.
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Walt Disney House

Learn about the local history of Chicago with a stop at Walt Disney House. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.
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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.
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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.
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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.
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The Gift Theatre

You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and acclaimed theatre scene in this vibrant area.
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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.
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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.
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What to do in Northwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

NZ$47
per adult
98% of travellers recommend
Flyover in Chicago
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 . 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.

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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.