Rp 1,966,393+ 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 27/10. 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 — DPS
11 Nov — 18 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 12 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
ChicagoLas Vegas
MDW Chicago Midway - LAS Las Vegas Harry Reid Intl
MDWLAS
Chicago Midway
Wed 25/11
17.15-19.15
Nonstop4h 00m
Las Vegas Harry Reid Intl
Wed 31/12
00.00-02.00
Nonstop0h 00m
Rp 2,055,774
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Thu 5/11
21.55-00.40
Nonstop4h 45m
Oakland
Wed 31/12
00.00-02.00
Nonstop0h 00m
Rp 2,073,650
ChicagoLas Vegas
MDW Chicago Midway - LAS Las Vegas Harry Reid Intl
MDWLAS
Chicago Midway
Sat 14/11
11.05-16.55
2 stops7h 50m
Las Vegas Harry Reid Intl
Wed 31/12
00.00-02.00
Nonstop0h 00m
Rp 2,145,156
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 7/11
10.25-17.05
1 stop8h 40m
Oakland
Wed 31/12
00.00-02.00
Nonstop0h 00m
Rp 2,252,413
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 23/12
07.35-12.20
1 stop6h 45m
San Francisco
Wed 31/12
00.00-02.00
Nonstop0h 00m
Rp 2,341,795
ChicagoEl Paso
MDW Chicago Midway - ELP El Paso
MDWELP
Chicago Midway
Thu 7/1
06.00-12.43
1 stop7h 43m
El Paso
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 2,520,558
ChicagoEl Paso
MDW Chicago Midway - ELP El Paso
MDWELP
Chicago Midway
Sat 9/1
06.00-12.43
1 stop7h 43m
El Paso
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 2,520,558
ChicagoEl Paso
MDW Chicago Midway - ELP El Paso
MDWELP
Chicago Midway
Wed 9/12
09.37-21.26
2 stops12h 49m
El Paso
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 2,609,939
ChicagoEl Paso
MDW Chicago Midway - ELP El Paso
MDWELP
Chicago Midway
Tue 8/12
12.39-21.26
2 stops9h 47m
El Paso
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 2,609,939
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Fri 8/1
13.00-21.44
1 stop7h 44m
Fort Myers SW Florida Intl
Wed 31/12
00.00-23.00
Nonstop0h 00m
Rp 2,699,321
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-DPS
MDW-LAS
MDW-RSW
MDW-SFO
MDW-YYC
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-DPS
MDW-LAS
MDW-RSW
MDW-SFO
MDW-YYC
What are popular destinations to fly to from Chicago Midway Airport?
From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (204 flights per day), Atlanta (171 flights per day) and Orlando (112 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 San Francisco, with prices starting at Rp 4,851,627. Explore other affordable destinations below.
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Other departure points
Other United States origins
Popular flights
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 12 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 12 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 12 October 2026.
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