£72+ Cheap flights from Chicago Midway Airport
This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 18/11. 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.
MDW — LHR
5 Nov — 12 Nov1
Find flights from Midway within your budget
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 6 October 2026. In the last 7 days, Cheapflights users made a total of 7,457,451 searches
Fly to
Route
Depart
Return
Cheapest return flight
ChicagoDenver
MDW Chicago Midway - DEN Denver Intl
MDWDEN
Chicago Midway
Wed 25/11
22:50-00:40
Nonstop2h 50m
Denver Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£72
ChicagoDenver
MDW Chicago Midway - DEN Denver Intl
MDWDEN
Chicago Midway
Thu 17/12
05:55-07:45
Nonstop2h 50m
Denver Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£76
ChicagoDenver
MDW Chicago Midway - DEN Denver Intl
MDWDEN
Chicago Midway
Thu 4/2
06:10-08:00
Nonstop2h 50m
Denver Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£76
Fastest return journey
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Wed 25/11
21:05-23:55
Nonstop1h 50m
Baltimore/Washington
Wed 31/12
00:00-23:00
Nonstop0h 00m
£79
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Wed 11/11
08:50-11:40
Nonstop1h 50m
Baltimore/Washington
Wed 31/12
00:00-23:00
Nonstop0h 00m
£80
ChicagoOrlando
MDW Chicago Midway - MCO Orlando
MDWMCO
Chicago Midway
Wed 18/11
16:25-20:00
Nonstop2h 35m
Orlando
Wed 31/12
00:00-23:00
Nonstop0h 00m
£83
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 20/1
06:25-12:25
1 stop5h 00m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£84
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 17/12
18:10-23:50
1 stop4h 40m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£84
ChicagoBaltimore
MDW Chicago Midway - BWI Baltimore/Washington
MDWBWI
Chicago Midway
Tue 15/12
17:12-01:07
1 stop6h 55m
Baltimore/Washington
Wed 31/12
00:00-23:00
Nonstop0h 00m
£88
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 24/11
12:50-23:30
1 stop9h 40m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£88
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway
Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
MDW-LHR
MDW-PHL
MDW-DEN
MDW-BWI
MDW-DCA
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.
Travel insights for flights from Midway
Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.
MDW-LHR
MDW-PHL
MDW-DEN
MDW-BWI
MDW-DCA
What are popular destinations to fly to from Chicago Midway Airport?
If you’re flying from Chicago Midway Airport, these routes are more frequently taken by airlines Orlando (130 flights per day), Detroit (112 flights per day) and Atlanta (86 flights per day).
What is the cheapest place to fly to from Chicago Midway Airport?
The cheapest city to fly to from Chicago Midway Airport is New York, with prices starting at £101. Explore other affordable destinations below.
Browse thousands of different options on Cheapflights for your next trip
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Alternate flight departure points to Midway
Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 6 October 2026.
Fly from other United States cities
Consider departing from one of these cities also located in United States. Flight origins are based on user searches made on Cheapflights and were last updated on 6 October 2026.
Popular Return Flight Destinations
Consider these popular destinations that Cheapflights users have chosen when departing from Chicago. Routes are based on user searches and were last updated on 6 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers in 2026
Related info for your journey
Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 6 October 2026.
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How does Cheapflights help users find flights from Midway?
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Can Cheapflights find flights from Midway with no change fees?
Yes! Cheapflights helps users easily find flights from Midway with no change fees.
Can Cheapflights notify me if prices for flights from Midway become cheaper?
Yes, Cheapflights offers price alerts on flights from Midway so you can book your travels when it’s right. The Price Alerts feature is available by clicking the bell icon next to the flight deals above and providing your email address.