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Cheap flights from London Heathrow Airport to Chicago Midway Airport from £408

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 23/3. Fares are subject to change and may not be available on all flights or dates of travel.
LHR — MDW
2 Jan — 9 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Heathrow to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Heathrow to Midway
Explore the most affordable flight options available from Heathrow to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 December 2025.

Tue 16/1206:30LHR - MDW
2 stops17h 30mDelta
Tue 13/113:49MDW - LHR
1 stop11h 16mDelta
Deal found 30/11£606
Mon 15/1211:05LHR - MDW
1 stop13h 13mKLM
Tue 13/113:49MDW - LHR
1 stop11h 16mKLM
Deal found 30/11£620
Mon 15/1213:05LHR - MDW
2 stops16h 42mVirgin Atlantic
Mon 12/106:45MDW - LHR
1 stop17h 40mVirgin Atlantic
Deal found 30/11£667
Tue 30/1211:45LHR - MDW
2 stops27h 20mKLM
Tue 6/113:49MDW - LHR
1 stop11h 16mKLM
Deal found 2/12£675
Tue 30/1206:30LHR - MDW
2 stops15h 50mDelta
Thu 29/112:48MDW - LHR
1 stop13h 02mDelta
Deal found 1/12£685
Tue 16/1215:50LHR - MDW
1 stop13h 57mVirgin Atlantic
Tue 23/1217:05MDW - LHR
1 stop31h 20mVirgin Atlantic
Deal found 1/12£688
Mon 15/1211:05LHR - MDW
1 stop13h 13mKLM
Sun 11/113:49MDW - LHR
1 stop11h 16mKLM
Deal found 30/11£697
Sat 27/1206:30LHR - MDW
2 stops16h 56mDelta
Sat 10/106:45MDW - LHR
1 stop17h 40mDelta
Deal found 3/12£712
Tue 30/1211:45LHR - MDW
2 stops27h 20mMultiple Airlines
Tue 6/111:21MDW - LHR
2 stops17h 29mMultiple Airlines
Deal found 2/12£713
Fri 26/1211:05LHR - MDW
1 stop12h 14mAir France
Mon 29/1218:08MDW - LHR
2 stops13h 37mAir France
Deal found 2/12£723
Fri 26/1211:05LHR - MDW
1 stop12h 14mDelta
Mon 29/1218:08MDW - LHR
2 stops13h 37mDelta
Deal found 2/12£726
Wed 17/1209:40LHR - MDW
2 stops20h 07mVirgin Atlantic
Wed 24/1209:29MDW - LHR
2 stops15h 16mVirgin Atlantic
Deal found 1/12£728

Find flight deals from Heathrow to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Heathrow (LHR) to Midway (MDW). 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 3 December 2025.

Round-trip from

£498

One-way from

£408

Popular in

July

Cheapest in

March

Average price

£788
Virgin Atlantic
  • Virgin Atlantic
  • 12/1-19/1
  • 2 total stops
  • 24h 43m total
  • London to Chicago
Search Deals
Virgin Atlantic
  • Virgin Atlantic
  • 23/3
  • 1 total stop
  • 12h 35m total
  • London to Chicago
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (£221 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease (£57 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Heathrow to Midway 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 858,174 searches. Data last updated 3 December 2025.
Use the filters below to find and compare flights from London Heathrow Airport to Chicago Midway Airport that are best for you.

Fly from

Heathrow

Fly to

Midway

Route

Depart

Return

Price

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Wed 21/1

06:30-17:29

2 stops16h 59m

Chicago Midway

Thu 29/1

13:26-08:05

2 stops12h 39m

£526

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Tue 17/2

08:40-18:37

2 stops15h 57m

Chicago Midway

Thu 26/2

13:49-07:05

1 stop11h 16m

£526

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Mon 9/2

06:20-18:36

2 stops18h 16m

Chicago Midway

Mon 16/2

10:53-06:25

1 stop13h 32m

£530

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Mon 16/2

11:05-18:37

1 stop13h 32m

Chicago Midway

Thu 26/2

13:49-07:05

1 stop11h 16m

£538

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Tue 17/2

10:45-17:45

1 stop13h 00m

Chicago Midway

Wed 25/2

18:40-11:40

1 stop11h 00m

£538

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Tue 27/1

08:55-17:29

1 stop14h 34m

Chicago Midway

Mon 20/4

13:05-06:30

1 stop11h 25m

£538

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Wed 28/1

08:55-17:29

1 stop14h 34m

Chicago Midway

Tue 21/4

13:05-06:30

1 stop11h 25m

£538

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Mon 26/1

10:45-22:22

1 stop17h 37m

Chicago Midway

Wed 22/4

13:05-06:30

1 stop11h 25m

£538

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Thu 22/1

08:40-18:36

2 stops15h 56m

Chicago Midway

Mon 26/1

10:46-06:50

2 stops14h 04m

£556

LondonChicago

LHR - MDW

LHRMDW

London Heathrow

Thu 22/1

08:40-17:55

2 stops15h 15m

Chicago Midway

Mon 26/1

13:26-08:45

1 stop13h 19m

£556

Flights are sorted by cheapest return flights first.

Deals found on 1/12

Showing 1-10 of 20 results
1
2

Best time to book a flight from Heathrow to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Heathrow with our price prediction graph.
Estimated return 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 Heathrow Airport to Chicago Midway Airport

What is the cheapest month to book a flight from London Heathrow Airport to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from London Heathrow Airport to Chicago Midway Airport (average of £426). Flying from London Heathrow Airport to Chicago Midway Airport in December is currently the most expensive (average of £788). 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated 3 December 2025.
See what other customers who have flown with Virgin Atlantic from London Heathrow Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Virgin Atlantic
7.5
Good
675 reviews
Check prices

Crew

8.2

Food

6.9

Entertainment

7.5

Overall

7.5

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
6.0
Good

Pratap,Aug 2025

JFK - LHR

The flight is clean, food good and the staff are excellent! Very professional, polite and accommodating. The seat itself is really mediocre. Can’t believe there is not inch of storage space. Believe it or not it there is not place even to put away your phone or pen!! Very very surprising and terribly inconvenient. No coat hanger hook either. Had to give it away. ALL IN ALL VERY INCONVENIENT business class seat compared to their peers. What is even more surprising is that this on their relatively new fleet of Airbus A350-1000. I was having com platelets different expectations of Virgin and this has disappointed me. Everything else is just as good and as you would expect from Virgin!
Virgin Atlantic
7.5
Good
675 reviews
Virgin Atlantic
7.5
Good
675 reviews
Check prices

Crew

8.2

Food

6.9

Entertainment

7.5

Overall

7.5

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
6.0
Good

Pratap,Aug 2025

JFK - LHR

The flight is clean, food good and the staff are excellent! Very professional, polite and accommodating. The seat itself is really mediocre. Can’t believe there is not inch of storage space. Believe it or not it there is not place even to put away your phone or pen!! Very very surprising and terribly inconvenient. No coat hanger hook either. Had to give it away. ALL IN ALL VERY INCONVENIENT business class seat compared to their peers. What is even more surprising is that this on their relatively new fleet of Airbus A350-1000. I was having com platelets different expectations of Virgin and this has disappointed me. Everything else is just as good and as you would expect from Virgin!

Related info for your journey

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

  • How long is the flight from London Heathrow Airport to Chicago Midway Airport?

    There are many flights that can get you from London Heathrow Airport to Chicago Midway Airport in 15h 57m. Fly via Virgin Atlantic or Delta to get the fastest option. Airlines will cover a distance of 3942 mi. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What is the cheapest airline to fly from London Heathrow Airport to Chicago Midway Airport round-trip?

    Currently priced at £434, Virgin Atlantic will fly you from London Heathrow Airport to Chicago Midway Airport and back. In addition to Virgin Atlantic, many other airlines offer competitively priced options for your trip. Virgin Atlantic is priced at 36% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Heathrow to Midway that include hotel bookings?

    Yes. In addition to deals on Heathrow to Midway flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Heathrow to Midway?

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

  • Can I find deals for business class flights from Heathrow to Midway?

    Yes. Cheapflights offers flight deals from Heathrow to Midway 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 Heathrow Airport to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from London Heathrow Airport to Chicago Midway Airport (average of £426). Flying from London Heathrow Airport to Chicago Midway Airport in December is currently the most expensive (average of £788). 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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Top airline flying from Heathrow to Midway

Discover the top airline that operate flights from Heathrow to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 3 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Virgin AtlanticCheapest£434Average£536FlexibilityNo cancel feeOn-time72%
Search Virgin Atlantic flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Heathrow to Midway?

Cheapflights helps you search for flights from Heathrow to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Heathrow to Midway?

Cheapflights helps you find that perfect flight to Midway from Heathrow 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 Heathrow to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Heathrow to Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Heathrow to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Heathrow to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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