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We work with hundreds of travel agencies and airlines to bring you the best airfare deals from MDW.
Good to Know: Cheapest and Fastest Flights from MDW
Useful information for finding cheap flights from Chicago Midway International and booking your next trip
Cheapest Round Trip Flight
$360
Southwest Airlines
• 1 stop
• 7h 30m
Jun 27 – Jun 27
The cheapest round trip flight from Chicago to Miami (MDW-MIA-MDW) is currently $360
Cheapest One way Flight
$167
Frontier Airlines
• 1 stop
• 15h 17m
Jun 28
The cheapest one way flight from Chicago to Los Angeles (MDW-LAX) is currently $167
Cheapest Direct Flight
$354
American Airlines
• nonstop
• 4h 2m
Jun 26
The cheapest nonstop flight from Chicago to St Petersburg-Clearwater (MDW-PIE) is currently $354
Fastest Flight
3h 25m
The fastest nonstop flight from Chicago to Oklahoma City (MDW-OKC) takes 3h 25m
Top Airlines Flying from Chicago Midway International (MDW)
Most Recent Flight Deals from Chicago Now!
Compare and book low fare round-trip air tickets from Chicago. Ideal for travelers with confirmed return itineraries.
Jun 27 - Jun 27, Economy
Chicago → Miami
7h 30m
6:35 AM - 12:25 PM • 1 stop
Chicago → Miami
10h 35m
5:30 PM - 11:05 PM • 1 stop
Southwest Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 13m
11:19 AM - 3:12 PM • nonstop
Chicago → St Petersburg-Clearwater
5h 10m
12:30 PM - 2:40 PM • nonstop
United Airlines
Jun 27 - Jun 27, Economy
Chicago → Miami
13h 35m
5:00 AM - 2:15 PM • 1 stop
Chicago → Miami
18h 45m
8:45 PM - 7:10 AM • 1 stop
Southwest Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
9h
6:00 PM - 12:40 AM • 1 stop
Chicago → St Petersburg-Clearwater
5h 11m
7:42 PM - 9:53 PM • nonstop
American Airlines
Jun 26 - Jun 27, Economy
Chicago → Oklahoma City
13h 20m
9:40 AM - 5:40 PM • 1 stop
Chicago → Oklahoma City
2h 30m
2:20 PM - 4:10 PM • nonstop
Southwest Airlines
Explore competitive one-way airfare options from Chicago. Best suited for flexible or open-ended travel plans.
Access real-time availability on last-minute departures from Chicago. Tailored for urgent or short-notice travel requirements.
Jun 27 - Jun 27, Economy
Chicago → Miami
7h 30m
6:35 AM - 12:25 PM • 1 stop
Chicago → Miami
10h 35m
5:30 PM - 11:05 PM • 1 stop
Southwest Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 13m
11:19 AM - 3:12 PM • nonstop
Chicago → St Petersburg-Clearwater
5h 10m
12:30 PM - 2:40 PM • nonstop
United Airlines
Jun 27 - Jun 27, Economy
Chicago → Miami
13h 35m
5:00 AM - 2:15 PM • 1 stop
Chicago → Miami
18h 45m
8:45 PM - 7:10 AM • 1 stop
Southwest Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
9h
6:00 PM - 12:40 AM • 1 stop
Chicago → St Petersburg-Clearwater
5h 11m
7:42 PM - 9:53 PM • nonstop
American Airlines
Jun 26 - Jun 27, Economy
Chicago → Oklahoma City
13h 20m
9:40 AM - 5:40 PM • 1 stop
Chicago → Oklahoma City
2h 30m
2:20 PM - 4:10 PM • nonstop
Southwest Airlines
Discover direct flight options from Chicago (MDW). Save time by avoiding layovers and reaching your destination directly.
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 2m
6:47 PM - 10:29 PM • nonstop
Chicago → St Petersburg-Clearwater
5h 10m
7:00 AM - 9:10 AM • nonstop
American Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 13m
5:56 PM - 9:49 PM • nonstop
Chicago → St Petersburg-Clearwater
5h 11m
7:42 PM - 9:53 PM • nonstop
United Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 13m
11:19 AM - 3:12 PM • nonstop
Chicago → St Petersburg-Clearwater
5h 10m
12:30 PM - 2:40 PM • nonstop
United Airlines
Jun 26 - Jun 30, Economy
Chicago → St Petersburg-Clearwater
4h 13m
7:31 AM - 11:24 AM • nonstop
Chicago → St Petersburg-Clearwater
5h 10m
12:30 PM - 2:40 PM • nonstop
United Airlines
Jun 26 - Jun 27, Economy
Chicago → Oklahoma City
3h 25m
10:10 AM - 12:15 PM • nonstop
Chicago → Oklahoma City
2h 30m
2:20 PM - 4:10 PM • nonstop
Southwest Airlines
FAQs on Flights from Chicago (MDW)
Which airlines fly from Chicago?
Airlines flying the most from Chicago (MDW)
What are the most popular destination from Chicago ( MDW )?
Travelers frequently travel to Los Angeles, Miami, Oklahoma City, St Petersburg-Clearwater from Chicago
Hotels near Chicago Midway International (MDW)
Doubletree By Hilton Hotel Chicago Alsip
5000 West 127th Street, Alsip, Illinois, 60803
Hyatt Regency McCormick Place
2233 S Martin Luther King Dr, Chicago, Illinois, 60616
MileNorth Hotel
166 E Superior Street, Chicago, Illinois, 60611
Sheraton Grand Chicago
301 E North Water St, Chicago, Illinois, 60611
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, Illinois, 60611
Airport Information: Chicago Midway International (MDW)
- IATA Code
- MDW
- Name
- Chicago Midway International
- City
- Chicago
- Country
- US
- Latitude
- 41.7859992980957
- Longitude
- -87.75240325927734
Chicago (MDW) Arrivals and Departures
| Airline | Flight code | Arrival time | Status |
|---|---|---|---|
Qatar Airways
QTR2A
|
B77L
|
23rd Jun, 2026 9:42 PM
|
Arriving |
|
American Airlines
AAL2596
|
B738
|
23rd Jun, 2026 9:42 PM
|
Arriving |
SkyWest Airlines
SKW5844
|
E75L
|
23rd Jun, 2026 9:52 PM
|
Arriving |
United Airlines
UAL254
|
B739
|
23rd Jun, 2026 9:41 PM
|
Arriving |
|
American Airlines
AAL1592
|
B738
|
23rd Jun, 2026 9:53 PM
|
Arriving |
|
SkyWest Airlines
SKW6274
|
CRJ7
|
23rd Jun, 2026 9:53 PM
|
Arriving |
Delta Airlines
DAL2130
|
BCS1
|
23rd Jun, 2026 9:53 PM
|
Arriving |
|
Southwest Airlines
SWA956
|
B737
|
23rd Jun, 2026 9:48 PM
|
Arriving |
|
Southwest Airlines
SWA998
|
B738
|
23rd Jun, 2026 9:48 PM
|
Arriving |
|
Southwest Airlines
SWA3766
|
B38M
|
23rd Jun, 2026 9:46 PM
|
Arriving |
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