Northwest Side Holidays from £1,354

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Top Northwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,868, price is now £1,354 per person
£1,354
per person
3 Aug - 8 Aug
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable

Reviewed on 26 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,950, price is now £1,374 per person
£1,374
per person
2 Aug - 7 Aug
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on 22 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £3,153, price is now £2,358 per person
£2,358
per person
4 Jul - 11 Jul
found 21 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast

Reviewed on 26 May 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,921, price is now £1,465 per person
£1,465
per person
2 Aug - 7 Aug
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,231 reviews)
I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back.

Reviewed on 25 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,350, price is now £1,801 per person
£1,801
per person
4 Jul - 11 Jul
found 21 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!

Reviewed on 26 May 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
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Irving Park

2 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 Irish American Heritage Center 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is £119 per night from 27 May to 28 May
£119
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is £179 per night from 27 May to 28 May
£179
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,252 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on 26 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £162 per night from 24 Jun to 25 Jun
£162
24 Jun - 25 Jun
includes taxes & fees
7.8/10 Good! (1,477 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on 26 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 5,073 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.
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Beach Holidays
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Family Friendly Holidays

Popular places to visit

Wrigley Field

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
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

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
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Northwest Side

Frequently asked questions

Can I cancel my flight booking to Northwest Side due to COVID-19?
Our Customer Service Portal is where you can find information about changing or cancelling your flight due to COVID-19. Before purchasing your tickets, it's smart to check the terms and conditions of your airfare too.
What's the best way to find cheap flights to Northwest Side that have flexible change policies?
We know that things can change from one minute to the next, so booking a flexible airfare with Expedia is always a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to Northwest Side is only a few clicks away.
What are some of the general tips for travellers to Northwest Side during the COVID-19 outbreak?
With the continuation of the COVID-19 outbreak, travelling now comes with more challenges than in the past. Cast your eye over these worthwhile tips before boarding your flight to Northwest Side:
  • Before you book a flight, check if any travel restrictions apply — in both your origin and destination. Get the latest updates by reviewing government and airport websites.
  • When you pass through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. This will need to be removed for screening.
  • To reduce handling during the screening process, place items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
  • If you're planning to take food through the security checkpoint, put it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA employee will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Northwest Side?
Arrange your ticket with American Airlines and then begin working on your Northwest Side itinerary. This popular carrier offers 13307 flights a month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Northwest Side?
An effective strategy for getting your hands on cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Northwest Side, then click on the "flexible dates" box for a list of prices for nearby days. Another good tip? Book ahead of time. For an idea of costs, was the lowest price for a flight to Northwest Side in the last seven days.
How much is a flight to Northwest Side?
If you were travelling one way from (), you could've nabbed a cheap ticket for in the last seven days. Round-trip flights to Northwest Side ranged from to during this same period.
What are the most popular airports to fly into in Northwest Side?
Get ready to pack your suitcase and jet into O'Hare Intl. Airport (ORD), Northwest Side's primary flight hub. Book a fare on one of the 33491 flights that land at this popular destination every month.
When is the cheapest time to fly to Northwest Side?
Fly out on a Tuesday to boost your odds of landing the cheapest flight to Northwest Side. Mondays are usually the second most affordable day to take off. Saturday is generally the most expensive day to fly anywhere.
How much is a plane ticket to Northwest Side?
In the last seven days, fares to Northwest Side fluctuated between and . The early bird catches the worm, so snap up a bargain today.
Which airlines with flights to Northwest Side employ COVID-19 cleanliness policies?
As travel bans start to lift, many airlines are now servicing flights with new strategies including physical distancing and staggered boarding and disembarkation. Here's what some carriers are doing to help combat COVID-19:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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. Flight-inclusive packages are ATOL protected.