LON - MDW

£381 Find Cheap Flights from London to Chicago Midway Airport – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from London to Chicago departing on 10/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest return fare
£507
Multiple Airlines
Sun 13/9Sun 20/9
LGW - MDW • 2 stops
Cheapest one-way flight
£381
Multiple Airlines
Thu 10/9
LGW - MDW • 1 stop
Top airlines
Cheapest • from £586 (return)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between London and Chicago. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top stopover airports
Cheapest • Avg £741 (return)
Shortest trip • 12h 20m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from London to Chicago (LON-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from London to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from London to Chicago

Sun, 13 Sep - Sun, 20 Sep
Multiple Airlines Logo
09:40 - 14:35
LGW
-
MDW
34h 55m
2 stops
Multiple Airlines Logo
11:45 - 07:55
MDW
-
LGW
14h 10m
2 stops
£507Multiple Airlines
Mon, 21 Sep - Sun, 27 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
11:45 - 07:55
MDW
-
LGW
14h 10m
2 stops
£509Multiple Airlines
Mon, 7 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
15:20 - 07:55
MDW
-
LGW
34h 35m
2 stops
£515Multiple Airlines
Mon, 7 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
15:20 - 07:55
MDW
-
LGW
34h 35m
2 stops
£518Multiple Airlines
Mon, 7 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
15:20 - 07:55
MDW
-
LGW
34h 35m
2 stops
£519Multiple Airlines
Sat, 19 Sep - Sun, 27 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
11:45 - 07:55
MDW
-
LGW
14h 10m
2 stops
£519Multiple Airlines
Mon, 7 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:35 - 14:35
LGW
-
MDW
33h 00m
2 stops
Multiple Airlines Logo
15:20 - 07:55
MDW
-
LGW
34h 35m
2 stops
£520Multiple Airlines
Mon, 14 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:35 - 11:00
LGW
-
MDW
29h 25m
2 stops
Multiple Airlines Logo
15:20 - 07:55
MDW
-
LGW
34h 35m
2 stops
£522Multiple Airlines
Tue, 8 Sep - Tue, 15 Sep
Virgin Atlantic Logo
20:55 - 16:57
LHR
-
MDW
26h 02m
2 stops
Virgin Atlantic Logo
09:29 - 10:20
MDW
-
LHR
18h 51m
2 stops
£586Virgin Atlantic
Wed, 9 Sep - Tue, 15 Sep
Virgin Atlantic Logo
08:40 - 18:19
LHR
-
MDW
15h 39m
2 stops
Virgin Atlantic Logo
13:19 - 10:20
MDW
-
LHR
15h 01m
2 stops
£586Virgin Atlantic
Booking Insights

KAYAK’s insights & trends for London to Chicago flights

Get data-powered insights and trends into flights from London to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a return flight from London to Chicago Midway Airport?

This analysis is based on the cheapest return trip price found on KAYAK in the last 12 months by searching for a flight from London to Chicago Midway Airport departing in September.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from London usually cost between £774 and £1,007 in September.
The lowest price found in the past 5 days was £507 on Multiple Airlines (13 Sept–20 Sept).

What is the cheapest month to fly from London to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from London to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from London to Chicago Midway Airport is February, where tickets cost £0 (return) on average. On the other hand, the most expensive months are September and December, where the average cost of round-trip tickets is £2,394 and £1,269 respectively.

Good to know - Cheap tickets from London to Chicago Midway Airport

Cheapest flight

£381
Most popular time to fly and prices are also 6% lower on average.
Flight from London Gatwick Airport to Chicago Midway Airport

When to book flights from London to Chicago

Are your dates flexible? Find out the best times to travel from London to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking London to Chicago Midway Airport flights

  • What is the cheapest flight from London to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from London to Chicago Midway Airport was £381 for a one-way ticket and £507 for a return.

  • Which airports will I be using when flying from London to Chicago Midway Airport?

    London has 4 major airports: London City, London Gatwick, London Heathrow, and London Luton. Chicago Midway is the only airport in Chicago Midway Airport. You’ll usually find the cheapest deals if you fly from London Heathrow Airport.

  • Which aircraft models fly most regularly from London to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from London to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between London and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from London to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from London to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from London to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from London is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from London to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago Midway Airport with an airline and back to London with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from London to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from London up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from London to Chicago

 
See real verified KAYAK customer reviews for airlines flying from London to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from London to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Virgin AtlanticOverall score based on 694 reviews
6.9Food
8.1Crew
7.3Comfort
7.7Boarding
7.5Entertainment
Airline reviews

Lounge was top notch h with great variety of food and drinks. Cabin crew were great. Smooth flight.

10.0 ExcellentLye Sim, Jun 2026
LHR - JFK
Read more Virgin Atlantic reviews

Lounge was top notch h with great variety of food and drinks. Cabin crew were great. Smooth flight.

My seat 3G did not go down fully and the buttons were not working properly

Food was the worst I’ve had on a VA flight. Normally it’s a lot better

The staff was not very polite but the flight was very very nice and comfortable and the entertainment was great

Security area in terminal 3 needs to be made much nicer. Less claustrophobic and use of glass and big ceilings wouldhelp

accomodating check in staff, friendly flight crew ( a crew member was speaking tactlessly and was overfamiliar with passengers

Seats need to be updated. Allowance needs to be made for dinner service at an alternative time

If I could fly Virgin Atlantic airlines to every place, I need to go, I would. Leaving Heathrow through the special virgin air entrance, security is completely white glove service. I love this airline. From ticketing agents to flight staff everyone tries to make it a wonderful & happy flight experience. I wish other airlines copied the positive culture of Virgin Airlines.

Premium was very comfortable. Food was delicious. I had specific diet requirement and Virgin Atlantic ensured it was provided. Onboard crew was very friendly and caring. Extremely smooth journey. I wonder how upper class experience would be. Perhaps one day, I will try upper class.

On arrival to JFK it to 3.5hrs to clear immigration, as only 3 booths open. Almost missed connection

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

Information on your arrival and departure airports