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Cheap flights from London, ON to Chicago from C$ 356

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 31/10. Fares are subject to change and may not be available on all flights or dates of travel.
YXU — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from London to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from London (YXU) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 17 September 2025.

Round-trip from

C$ 512

One-way from

C$ 356
WestJet
  • WestJet
  • 22/10-25/10
  • 2 total stops
  • 46h 25m total
  • London to Chicago
Search Deals
Air Canada
  • Air Canada
  • 31/10
  • 1 total stop
  • 6h 45m total
  • London to Chicago
Search Deals

Find flight deals from London to Chicago

Cheapest flights from London to Chicago
Explore the most affordable flight options available from London to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2025.

Wed 22/108:00 p.m.YXU - ORD
1 stop21h 43mWestJet
Sat 25/105:30 p.m.ORD - YXU
1 stop24h 42mWestJet
Deal found 16/9C$ 512
Wed 22/106:00 a.m.YXU - ORD
2 stops18h 59mMultiple Airlines
Sat 25/105:30 p.m.ORD - YXU
1 stop24h 42mMultiple Airlines
Deal found 16/9C$ 597
Fri 7/119:25 a.m.YXU - ORD
1 stop6h 45mAir Canada
Mon 10/1110:00 a.m.ORD - YXU
1 stop6h 05mAir Canada
Deal found 16/9C$ 656
Wed 3/125:15 a.m.YXU - ORD
1 stop4h 58mAir Canada
Sat 6/122:00 p.m.ORD - YXU
1 stop6h 21mAir Canada
Deal found 16/9C$ 658
Wed 22/109:55 a.m.YXU - ORD
2 stops11h 22mAir Canada
Sat 25/1010:40 a.m.ORD - YXU
2 stops9h 47mAir Canada
Deal found 16/9C$ 671
Wed 3/128:10 p.m.YXU - ORD
2 stops24h 06mMultiple Airlines
Sat 6/127:35 a.m.ORD - YXU
3 stops34h 37mMultiple Airlines
Deal found 16/9C$ 773
Tue 14/109:55 a.m.YXU - ORD
2 stops14h 20mUnited Airlines
Tue 21/107:10 a.m.ORD - YXU
2 stops13h 17mUnited Airlines
Deal found 16/9C$ 812
Wed 22/108:00 p.m.YXU - MDW
2 stops21h 24mMultiple Airlines
Sat 25/109:20 a.m.MDW - YXU
3 stops32h 52mMultiple Airlines
Deal found 16/9C$ 941
Wed 3/128:10 p.m.YXU - MDW
3 stops20h 10mMultiple Airlines
Sat 6/121:50 p.m.MDW - YXU
3 stops28h 22mMultiple Airlines
Deal found 16/9C$ 1,034
Wed 22/106:00 a.m.YXU - MDW
3 stops32h 08mWestJet
Sat 25/109:20 a.m.MDW - YXU
3 stops32h 52mWestJet
Deal found 16/9C$ 1,040
Wed 3/128:10 p.m.YXU - MDW
2 stops17h 58mWestJet
Sat 6/1211:05 a.m.MDW - YXU
2 stops31h 07mWestJet
Deal found 16/9C$ 2,063
Fri 7/118:10 p.m.YXU - MDW
2 stops17h 58mWestJet
Mon 10/111:47 p.m.MDW - YXU
2 stops28h 25mWestJet
Deal found 16/9C$ 2,158

Cheapflights Fare Finder

 
Customize your flight search to find flights from London to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 17 September 2025.
Use the filters below to find and compare flights from London to Chicago that are best for you.

Fly from

London

Fly to

Chicago

Route

Depart

Return

Price

LondonChicago

YXU - ORD

YXUORD

London

Wed 22/10

8:00 p.m.-4:43 p.m.

1 stop21h 43m

Chicago O'Hare Intl

Sat 25/10

5:30 p.m.-7:12 p.m.

1 stop24h 42m

C$ 512

LondonChicago

YXU - ORD

YXUORD

London

Wed 22/10

6:00 a.m.-11:59 p.m.

2 stops18h 59m

Chicago O'Hare Intl

Sat 25/10

5:30 p.m.-7:12 p.m.

1 stop24h 42m

C$ 597

LondonChicago

YXU - ORD

YXUORD

London

Wed 3/12

5:15 a.m.-9:13 a.m.

1 stop4h 58m

Chicago O'Hare Intl

Sat 6/12

2:00 p.m.-9:21 p.m.

1 stop6h 21m

C$ 658

LondonChicago

YXU - ORD

YXUORD

London

Wed 22/10

9:55 a.m.-8:17 p.m.

2 stops11h 22m

Chicago O'Hare Intl

Sat 25/10

10:40 a.m.-9:27 p.m.

2 stops9h 47m

C$ 671

LondonChicago

YXU - ORD

YXUORD

London

Fri 7/11

9:25 a.m.-3:10 p.m.

1 stop6h 45m

Chicago O'Hare Intl

Mon 10/11

7:15 a.m.-5:05 p.m.

2 stops8h 50m

C$ 685

LondonChicago

YXU - ORD

YXUORD

London

Wed 3/12

8:10 p.m.-7:16 p.m.

2 stops24h 06m

Chicago O'Hare Intl

Sat 6/12

7:35 a.m.-7:12 p.m.

3 stops34h 37m

C$ 773

LondonChicago

YXU - ORD

YXUORD

London

Tue 14/10

9:55 a.m.-11:15 p.m.

2 stops14h 20m

Chicago O'Hare Intl

Tue 21/10

7:10 a.m.-9:27 p.m.

2 stops13h 17m

C$ 812

LondonChicago

YXU - MDW

YXUMDW

London

Wed 22/10

8:00 p.m.-4:24 p.m.

2 stops21h 24m

Chicago Midway

Sat 25/10

9:20 a.m.-7:12 p.m.

3 stops32h 52m

C$ 941

LondonChicago

YXU - MDW

YXUMDW

London

Wed 3/12

8:10 p.m.-3:20 p.m.

3 stops20h 10m

Chicago Midway

Sat 6/12

1:50 p.m.-7:12 p.m.

3 stops28h 22m

C$ 1,034

LondonChicago

YXU - MDW

YXUMDW

London

Wed 22/10

6:00 a.m.-1:08 p.m.

3 stops32h 08m

Chicago Midway

Sat 25/10

9:20 a.m.-7:12 p.m.

3 stops32h 52m

C$ 1,040

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 20 results
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2

Best time to book a flight from London to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from London with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from London to Chicago

What is the cheapest month to book a flight from London, Ontario to Chicago?

Currently, January is the cheapest month in which you can book a flight from London, Ontario to Chicago (average of C$ 261). Flying from London, Ontario to Chicago in March is currently the most expensive (average of C$ 348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What’s the top layover airport for flights from London, Ontario to Chicago?

Share of one-stop round-trip flights from London, Ontario to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 83% of one-stop itineraries from London, Ontario to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from London, Ontario to Chicago?

Average round-trip fare for 1-stop flights from London, Ontario to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 471.

What’s the fastest layover option from London, Ontario to Chicago?

Shortest average travel time for 1-stop one-way flights from London, Ontario to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 4h 00m.

Which airport typically offers the quickest layover for flights from London, Ontario to Chicago?

Average layover duration for 1-stop one-way flights from London, Ontario to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 32m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 17 September 2025.
Read through reviews of airlines operating flights from London to Chicago, such as Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Food

6.3

Overall

7.1

Comfort

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Food

6.3

Overall

7.1

Comfort

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.

Related info for your journey

Find useful and relevant information for your journey from London to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from London to Chicago?

    If you book a flight to Chicago from London, you will be flying from London, which is the city’s only airport. London (YXU) is located 8.6 km from the centre of London. There are 0 flights from London to Chicago per day from 0 different airlines.

  • How long is the flight from London, Ontario to Chicago?

    For as low as C$ 658, WestJet can have you in Chicago from London, Ontario in 4h 58m. Airlines will cover a distance of 565 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from London to Chicago that include hotel bookings?

    Yes. In addition to deals on London to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from London to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from London to Chicago.

  • Can I find deals for business class flights from London to Chicago?

    Yes. Cheapflights offers flight deals from London to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from London, Ontario to Chicago?

    Currently, January is the cheapest month in which you can book a flight from London, Ontario to Chicago (average of C$ 261). Flying from London, Ontario to Chicago in March is currently the most expensive (average of C$ 348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for London to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Fly with Cheapflights

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How does Cheapflights help users find flights from London to Chicago?

Deals for London to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from London to Chicago?

Cheapflights helps you find that perfect flight to Chicago from London by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from London to Chicago with no change fees?

Certainly. Search results for flights to Chicago from London shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from London to Chicago become cheaper?

Yes, Cheapflights offers price alerts on London to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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