Northwest Side Holidays from £1,045

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    Packages with flights are ATOL protected

Top Northwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was £1,508, price is now £1,045 per person
£1,045
per person
20 Sept - 25 Sept
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,081, price is now £1,334 per person
£1,334
per person
20 Sept - 25 Sept
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was £1,723, price is now £1,158 per person
£1,158
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on 18 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,626, price is now £1,095 per person
£1,095
per person
3 Oct - 10 Oct
found 6 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,636, price is now £1,118 per person
£1,118
per person
3 Oct - 10 Oct
found 6 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,336 reviews)
No hot water in the shower for the entirety of our 3 night stay, it was barely warm. Complained multiple times, other guests were also facing the same problem. The responses ranged from "engineers are working on it" to "leave the water running for longer" to finally "that is the hottest water you're going to get". That was unbelievable given that the sink had hotter water than the shower. Upon my insistence, they offered to move us to a different room the next day after 3pm - that meant we would have had to take cold showers for 2 days. In the end we just didn't take up the moving-rooms hassle in the middle of our trip.

Reviewed on 18 Aug 2025

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
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.

Find hotels in Irving Park

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

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £94 per night from 24 Aug to 25 Aug
£94
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 1 Sept to 2 Sept
£132
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is £133 per night from 3 Sept to 4 Sept
£133
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,031 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest Side

Frequently asked questions

How much does a Northwest Side travel package cost?
Our Northwest Side packages, which begin at just £1,045, 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.

* 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.