Northwest Side Holidays from £1,257

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    Save up to £750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,872, price is now £1,257 per person
£1,257
per person
11 Sept - 16 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,339, price is now £1,467 per person
£1,467
per person
12 Sept - 18 Sept
found 5 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.

Reviewed on 9 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was £2,144, price is now £1,404 per person
£1,404
per person
11 Sept - 18 Sept
found 5 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Loved the size of our room and how clean it was.

Reviewed on 9 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,134, price is now £1,406 per person
£1,406
per person
11 Sept - 16 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,951, price is now £1,320 per person
£1,320
per person
11 Sept - 16 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 2026

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 COLOR CLUB 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

Northwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in Northwest Side

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £223 per night from 26 Jul to 27 Jul
£223
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,900 reviews)
"Great hotel"

Reviewed on 10 Jul 2026

Omni Chicago 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 £136 per night from 27 Jul to 28 Jul
£136
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,729 reviews)
"The overall experience was a 7/10 . The rooms are only cleaned every 3 days . Great location ; several stores and restaurants are in walking distance ."

Reviewed on 10 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 £168 per night from 10 Aug to 11 Aug
£168
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,220 reviews)
"Only complaint showers with out doors are strange"

Reviewed on 10 Jul 2026

Congress Plaza Hotel
See all 4,812 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

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
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 £1,257, 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

* 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.