Northwest Side Holidays from £821
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Top Northwest Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
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
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.
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.
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.
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.
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.
Northwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top hotels in Northwest Side
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£104
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,143 reviews)
"Really bad hotel. The rooms are old and smell, they are also tiny. If you ask for housekeeping- 50/50 chance that they visit. If you need room service, they will be rude on the call and their usual answer is ‘it will take an hour or longer’ even if you need something simple. Only one elevator works. ..."
Reviewed on 9 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
£137
25 Oct - 26 Oct
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£128
10 Nov - 11 Nov
includes taxes & fees
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.
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.
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.
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.
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.
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.
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.
Michella Terrace Banquet Rooms
Michella Terrace Banquet Rooms is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels?
What to do in Northwest Side
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
Frequently asked questions
How much does a Northwest Side travel package cost?
Our Northwest Side packages, which begin at just £821, are an ideal way to save money. Pick your preferred hotels, flights and more to create your perfect getaway.
If I'm not able to travel, can I cancel my Northwest Side travel package?
Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Northwest Side travel package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If your circumstances suddenly change, look up our Customer Service Portal for more information.
How do I get a cheap travel package to Northwest Side?
Just imagine all the wonderful things you could do in Northwest Side with extra cash in your pocket. Watch your savings stack up when you combine your flights, hotels and extras into a Northwest Side holiday package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can pick from more than 550 air carriers and 1,000,000 hotel options across the globe. Whether you're taking off with the family or embarking on a solo adventure, planning a trip to Northwest Side is better with a package.
Does Expedia offer Book Now, Pay Later Northwest Side holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on the purse strings. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits into your budget. Consider these flexible payment options:
- Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all budgets, so you can take that well-deserved holiday now.
- Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.
How far in advance should I book my Northwest Side holiday?
To bag cheap prices, book nice and early. Airlines generally start selling tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Northwest Side, there are always plenty of great deals to be had on Expedia. Check them out now!
What does an Expedia Northwest Side travel package include?
Flights, hotels and rental cars, or any combination of them — it's up to you! Whether you're headed to Northwest Side with the kids or adventuring solo, there's a bundle to suit your style and budget. Once you've made your booking, why not add on one or two activities?
What should I know before booking a Northwest Side travel package?
Whether it's adventure or relaxation you're after, a Northwest Side travel package lets you plan your escape your way. Plus, you'll score great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Northwest Side Expedia travel package?
Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 airline partners all over the world, so you have lots of choice when planning your Northwest Side adventure.
Explore a world of travel with Expedia
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- Art Institute of Chicago
- Visit Bucktown
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- Chicago Theatre
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- Chicago Holidays
- Visit Chicago
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- Lincoln Hall
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- Michigan Avenue
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- Navy Pier
- Northwestern University
- Visit Oak Park
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- Shops at North Bridge
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- Unity Temple
- Willis Tower
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
