$59+ Cheap flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway (MDW)
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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Jun 17 — Jun 241
Round-trip
1 adult, Economy
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Cheapest flights from Detroit to MidwayExplore the most affordable flight options available from Detroit to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.
Explore the most affordable flight options available from Detroit to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:45 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Tue 9/298:35 am
MDW
- DTW
Nonstop1h 20m
Southwest
Deal found 5/15![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:35 am
DTW
- MDW
1 stop6h 25m
Southwest
Wed 6/105:30 pm
MDW
- DTW
1 stop4h 20m
Southwest
Deal found 5/14![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:07 pm
DTW
- MDW
Nonstop1h 24m
Delta
Tue 6/239:17 am
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/14![Delta logo]()
$187
This Frontier deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:02 pm
DTW
- MDW
1 stop9h 09m
Frontier
Wed 9/212:04 pm
MDW
- DTW
1 stop11h 38m
Frontier
Deal found 5/15![Frontier logo]()
$190
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:27 pm
DTW
- MDW
Nonstop1h 15m
Delta
Mon 6/86:58 pm
MDW
- DTW
Nonstop1h 21m
Delta
Deal found 5/13![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:50 am
DTW
- MDW
Nonstop1h 24m
Delta
Tue 7/71:18 pm
MDW
- DTW
Nonstop1h 17m
Delta
Deal found 5/17![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:25 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Mon 7/276:00 pm
MDW
- DTW
1 stop3h 25m
Southwest
Deal found 5/13![Southwest logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:38 pm
DTW
- MDW
1 stop18h 34m
Frontier
Mon 7/66:00 am
MDW
- DTW
1 stop17h 40m
Frontier
Deal found 5/15![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:35 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Mon 6/85:05 pm
MDW
- DTW
1 stop6h 00m
Southwest
Deal found 5/13![Southwest logo]()
$201
Best flights from Detroit to MidwayDiscover carefully curated flight deals from Detroit to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 18, 2026.
Discover carefully curated flight deals from Detroit to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 18, 2026.
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:20 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Sat 7/47:10 am
MDW
- DTW
1 stop4h 25m
Southwest
Deal found 5/13![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:15 pm
DTW
- MDW
Nonstop1h 16m
Delta
Mon 9/79:30 am
MDW
- DTW
Nonstop1h 10m
Delta
Deal found 5/17![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:50 am
DTW
- MDW
1 stop5h 50m
Southwest
Mon 6/85:05 pm
MDW
- DTW
1 stop6h 00m
Southwest
Deal found 5/13![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/223:50 pm
DTW
- MDW
1 stop4h 45m
Southwest
Sun 7/263:05 pm
MDW
- DTW
2 stops8h 00m
Southwest
Deal found 5/15![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:50 am
DTW
- MDW
Nonstop1h 24m
Delta
Sun 7/56:58 pm
MDW
- DTW
Nonstop1h 21m
Delta
Deal found 5/17![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:20 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Sun 8/237:55 am
MDW
- DTW
1 stop3h 45m
Southwest
Deal found 5/14![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:20 pm
DTW
- MDW
Nonstop1h 18m
Delta
Mon 8/31:27 pm
MDW
- DTW
Nonstop1h 17m
Delta
Deal found 5/17![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:25 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Sun 6/77:45 pm
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 5/14![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:20 pm
DTW
- MDW
Nonstop1h 18m
Delta
Sun 7/129:19 am
MDW
- DTW
Nonstop1h 16m
Delta
Deal found 5/17![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:00 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Thu 6/186:00 pm
MDW
- DTW
1 stop3h 25m
Southwest
Deal found 5/14![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:25 pm
DTW
- MDW
Nonstop1h 21m
Delta
Mon 6/299:17 am
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/15![Delta logo]()
$315
Last-minute flights from Detroit to MidwayDiscover last-minute flight deals from Detroit to Midway. Data last updated May 18, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Midway. Data last updated May 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:27 pm
DTW
- MDW
Nonstop1h 15m
Delta
Mon 6/86:58 pm
MDW
- DTW
Nonstop1h 21m
Delta
Deal found 5/13![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:35 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Mon 6/85:05 pm
MDW
- DTW
1 stop6h 00m
Southwest
Deal found 5/13![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:15 pm
DTW
- MDW
1 stop3h 45m
Southwest
Wed 6/105:30 pm
MDW
- DTW
1 stop4h 20m
Southwest
Deal found 5/14![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:05 am
DTW
- MDW
1 stop6h 55m
Southwest
Tue 6/94:10 pm
MDW
- DTW
1 stop5h 40m
Southwest
Deal found 5/13![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:20 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Wed 6/1012:55 pm
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 5/16![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:35 am
DTW
- MDW
1 stop6h 25m
Southwest
Wed 6/105:30 pm
MDW
- DTW
1 stop4h 20m
Southwest
Deal found 5/14![Southwest logo]()
$172
This Expedia deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:38 pm
DTW
- MDW
1 stop5h 33m
Frontier
Tue 6/2312:27 pm
MDW
- DTW
1 stop11h 17m
Frontier
Deal found 5/15![Frontier logo]()
$190
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:07 pm
DTW
- MDW
Nonstop1h 24m
Delta
Tue 6/239:17 am
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/14![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:25 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Tue 6/236:10 pm
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 5/16![Southwest logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:38 pm
DTW
- MDW
1 stop18h 34m
Frontier
Mon 7/66:00 am
MDW
- DTW
1 stop17h 40m
Frontier
Deal found 5/15![Frontier logo]()
$200
This KAYAK deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:50 am
DTW
- MDW
Nonstop1h 24m
Delta
Tue 6/309:17 am
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/13![Delta logo]()
$205
One-way flights from Detroit to MidwaySearch for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
Search for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated May 18, 2026.
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:25 pm
DTW
- MDW
Nonstop1h 21m
Delta
Deal found 5/13![Delta logo]()
$59
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:25 pm
DTW
- MDW
Nonstop1h 21m
Delta
Deal found 5/17![Delta logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:54 pm
DTW
- MDW
1 stop28h 17m
Frontier
Deal found 5/13![Frontier logo]()
$70
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:10 pm
DTW
- MDW
1 stop4h 00m
Southwest
Deal found 5/17![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:54 pm
DTW
- MDW
1 stop8h 14m
Frontier
Deal found 5/14![Frontier logo]()
$81
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:35 pm
DTW
- MDW
2 stops5h 35m
Southwest
Deal found 5/17![Southwest logo]()
$84
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:35 am
DTW
- MDW
2 stops9h 55m
Southwest
Deal found 5/15![Southwest logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:40 pm
DTW
- MDW
1 stop8h 31m
Frontier
Deal found 5/17![Frontier logo]()
$94
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:38 pm
DTW
- MDW
1 stop5h 30m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:21 pm
DTW
- MDW
Nonstop1h 18m
Delta
Deal found 5/13![Delta logo]()
$96
This Frontier deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:02 pm
DTW
- MDW
1 stop9h 06m
Frontier
Deal found 5/16![Frontier logo]()
$101
Find flight deals from Detroit to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTW) 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 May 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $164 (Southwest) |
One-way from | $59 (Delta) |
Popular in | February |
Cheapest in | January |
Average price | $339 |
Good round-trip deal | $396 or less |
Good one-way deal | $230 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Detroit 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 2,558,603 searches. Data last updated May 18, 2026.
Use the filters below to find and compare flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 6/27
7:20 pm-7:30 pm
Nonstop1h 10m
Chicago Midway
Sat 7/4
7:10 am-12:35 pm
1 stop4h 25m
$233
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 6/4
5:50 am-10:40 am
1 stop5h 50m
Chicago Midway
Mon 6/8
5:05 pm-12:05 am
1 stop6h 00m
$244
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Wed 7/22
3:50 pm-7:35 pm
1 stop4h 45m
Chicago Midway
Sun 7/26
3:05 pm-12:05 am
2 stops8h 00m
$251
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 9/5
6:15 pm-6:31 pm
Nonstop1h 16m
Chicago Midway
Mon 9/7
9:30 am-11:40 am
Nonstop1h 10m
$253
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 8/20
1:20 pm-1:30 pm
Nonstop1h 10m
Chicago Midway
Sun 8/23
7:55 am-12:40 pm
1 stop3h 45m
$263
Quickest round-trip
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 6/4
1:25 pm-1:35 pm
Nonstop1h 10m
Chicago Midway
Sun 6/7
7:45 pm-9:55 pm
Nonstop1h 10m
$266
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Fri 5/29
1:00 pm-1:10 pm
Nonstop1h 10m
Chicago Midway
Thu 6/18
6:00 pm-10:25 pm
1 stop3h 25m
$266
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Fri 7/3
8:50 am-9:14 am
Nonstop1h 24m
Chicago Midway
Sun 7/5
6:58 pm-9:19 pm
Nonstop1h 21m
$282
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 7/30
12:20 pm-12:38 pm
Nonstop1h 18m
Chicago Midway
Mon 8/3
1:27 pm-3:44 pm
Nonstop1h 17m
$315
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 7/9
12:20 pm-12:38 pm
Nonstop1h 18m
Chicago Midway
Sun 7/12
9:19 am-11:35 am
Nonstop1h 16m
$315
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Detroit to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Detroit to Midway in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Detroit to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Detroit with our price prediction graph.
DTW-MDW
Estimated round-trip 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.
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Everything you need to know about your flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport
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Airlines
What is the cheapest month to book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (average of $171). Flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in February is currently the most expensive (average of $469). 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.
What is the cheapest time of day to fly from DTW to MDW?
Find hourly flight availability from Detroit to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 18, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Detroit to Midway. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Detroit Metropolitan Wayne County Airport to Chicago Midway Airport trip
Our travel experts
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 May 18, 2026.
Read through reviews of airlines operating flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Detroit to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 18, 2026.
Detroit and Midway flights
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Top 2 airlines flying from Detroit to Midway
Discover the top 2 airlines that operate flights from Detroit 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 2,558,603 searches. Data last updated May 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$313 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$121 | Average$287 | FlexibilityNo cancel fee | On-timeN/A |