Northwest Side Holidays

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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 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.

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 Rp2.839.252 per night from 30 Aug to 31 Aug
Rp2.839.252
Rp3.375.587 total
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (10,214 reviews)
"Know that this is a very old hotel that hasn't seen a material renovation in decades. AC system is ancient, TVs are tiny. No overhead lighting. Blue tile bathroom with rusty fixtures. But the rooms are big and ours had walk in closets. And great location."

Reviewed on 6 Aug 2026

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 Rp2.725.278 per night from 24 Aug to 25 Aug
Rp2.725.278
Rp3.240.084 total
24 Aug - 25 Aug
includes taxes & fees
8/10 Very good! (1,930 reviews)
"Always love staying at the ambassador! So much old charm but modern amenities and gorgeous design. Located in a lovely quiet neighborhood north of the loop with lots of walkable cafes and restaurants."

Reviewed on 6 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is Rp3.046.563 per night from 30 Aug to 31 Aug
Rp3.046.563
Rp3.472.541 total
30 Aug - 31 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 4,887 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

What to do in Northwest Side

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Rp756.150
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp487.755
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

Rp443.676
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.