$104+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Detroit to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 June 23, 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 June 23, 2026.
This Frontier deal was found by Cheapflights users on 6/20. 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 8/46:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Tue 8/116:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/20![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 6/21. 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.
Wed 8/55:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Wed 8/126:05 am
MDW
- DTW
1 stop9h 23m
Frontier
Deal found 6/21![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 6/20. 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 7/282:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Tue 8/46:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/20![Frontier logo]()
$220
This Travelocity deal was found by Cheapflights users on 6/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Wed 8/56:05 am
MDW
- DTW
1 stop9h 23m
Frontier
Deal found 6/21![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 6/21. 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.
Tue 7/212:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Tue 7/2812:11 pm
MDW
- DTW
1 stop11h 29m
Frontier
Deal found 6/21![Frontier logo]()
$230
This Expedia deal was found by Cheapflights users on 6/20. 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 7/225:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Thu 7/2312:11 pm
MDW
- DTW
1 stop11h 29m
Frontier
Deal found 6/20![Frontier logo]()
$236
This Trip.com deal was found by Cheapflights users on 6/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Tue 7/216:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/22![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 6/19. 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.
Sat 8/82:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Mon 8/106:05 am
MDW
- DTW
1 stop9h 35m
Frontier
Deal found 6/19![Frontier logo]()
$240
This Expedia deal was found by Cheapflights users on 6/20. 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.
Fri 7/315:35 pm
DTW
- MDW
1 stop5h 28m
Frontier
Mon 8/36:05 am
MDW
- DTW
1 stop9h 35m
Frontier
Deal found 6/20![Frontier logo]()
$242
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 June 23, 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 June 23, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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 9/198:30 am
DTW
- MDW
Nonstop1h 15m
Southwest
Sat 9/193:25 pm
MDW
- DTW
Nonstop1h 05m
Southwest
Deal found 6/18![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 6/21. 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 8/88:54 am
DTW
- MDW
Nonstop1h 23m
Delta
Mon 8/101:25 pm
MDW
- DTW
Nonstop1h 17m
Delta
Deal found 6/21![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 6/19. 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 7/217:50 pm
DTW
- MDW
Nonstop1h 15m
Southwest
Sat 8/18:00 am
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 6/19![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 6/20. 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 8/84:45 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Mon 8/108:15 am
MDW
- DTW
Nonstop1h 15m
Southwest
Deal found 6/20![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/22. 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 7/276:07 pm
DTW
- MDW
Nonstop1h 18m
Delta
Wed 7/296:58 pm
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 6/22![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 6/20. 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 8/84:45 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Tue 8/116:30 am
MDW
- DTW
1 stop4h 50m
Southwest
Deal found 6/20![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 6/18. 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 8/68:55 am
DTW
- MDW
Nonstop1h 20m
Southwest
Mon 8/108:15 am
MDW
- DTW
Nonstop1h 15m
Southwest
Deal found 6/18![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 6/18. 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 7/213:50 pm
DTW
- MDW
1 stop4h 45m
Southwest
Thu 7/236:50 pm
MDW
- DTW
Nonstop1h 15m
Southwest
Deal found 6/18![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 6/20. 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 stop6h 50m
Southwest
Thu 7/237:55 am
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 6/20![Southwest logo]()
$289
Last-minute flights from Detroit to MidwayDiscover last-minute flight deals from Detroit to Midway. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Midway. Data last updated June 23, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Tue 7/216:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/22![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 6/19. 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.
Fri 7/175:35 pm
DTW
- MDW
1 stop5h 28m
Frontier
Fri 7/246:05 am
MDW
- DTW
1 stop9h 35m
Frontier
Deal found 6/19![Frontier logo]()
$241
This Trip.com deal was found by Cheapflights users on 6/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Wed 7/226:05 am
MDW
- DTW
1 stop9h 23m
Frontier
Deal found 6/23![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 6/23. 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 7/212:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Wed 7/296:05 am
MDW
- DTW
1 stop9h 23m
Frontier
Deal found 6/23![Frontier logo]()
$230
This Trip.com deal was found by Cheapflights users on 6/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Tue 7/286:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/23![Frontier logo]()
$238
This Delta deal was found by Cheapflights users on 6/23. 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 7/218:50 am
DTW
- MDW
Nonstop1h 23m
Delta
Wed 7/299:19 am
MDW
- DTW
Nonstop1h 16m
Delta
Deal found 6/23![Delta logo]()
$243
This Trip.com deal was found by Cheapflights users on 6/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Thu 8/66:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/21![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 6/23. 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.
Wed 7/226:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Thu 7/2312:11 pm
MDW
- DTW
1 stop11h 29m
Frontier
Deal found 6/23![Frontier logo]()
$236
This Trip.com deal was found by Cheapflights users on 6/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Wed 7/296:05 am
MDW
- DTW
1 stop9h 23m
Frontier
Deal found 6/21![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 6/23. 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.
Fri 7/246:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Sat 7/256:05 am
MDW
- DTW
1 stop6h 39m
Frontier
Deal found 6/23![Frontier logo]()
$242
This Super.com deal was found by Cheapflights users on 6/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Tue 8/46:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/22![Frontier logo]()
$220
This Trip.com deal was found by Cheapflights users on 6/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Tue 8/46:05 am
MDW
- DTW
1 stop6h 28m
Frontier
Deal found 6/22![Frontier logo]()
$226
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 June 23, 2026.
Search for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Super.com deal was found by Cheapflights users on 6/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Deal found 6/18![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 6/22. 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 8/55:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Deal found 6/22![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/20. 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 8/46:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Deal found 6/20![Frontier logo]()
$106
This Trip.com deal was found by Cheapflights users on 6/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Deal found 6/19![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 9/156:50 am
DTW
- MDW
1 stop16h 08m
Frontier
Deal found 6/19![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 6/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:56 pm
DTW
- MDW
1 stop8h 07m
Frontier
Deal found 6/23![Frontier logo]()
$114
This Expedia deal was found by Cheapflights users on 6/21. 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 7/155:13 pm
DTW
- MDW
1 stop5h 50m
Frontier
Deal found 6/21![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 6/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:10 am
DTW
- MDW
1 stop5h 57m
Frontier
Deal found 6/23![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 6/22. 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.
Fri 7/245:35 pm
DTW
- MDW
1 stop5h 28m
Frontier
Deal found 6/22![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 6/22. 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
Deal found 6/22![Southwest logo]()
$122
This Expedia deal was found by Cheapflights users on 6/22. 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.
Mon 7/275:35 pm
DTW
- MDW
1 stop5h 28m
Frontier
Deal found 6/22![Frontier logo]()
$124
This Expedia deal was found by Cheapflights users on 6/20. 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.
Fri 7/1011:49 am
DTW
- MDW
1 stop6h 33m
Frontier
Deal found 6/20![Frontier logo]()
$126
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Frontier) |
One-way from | $104 (Super.com) |
Popular in | February |
Cheapest in | January |
Average price | $397 |
Good round-trip deal | $350 or less |
Good one-way deal | $222 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 June 23, 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
Quickest round-trip
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 9/19
8:30 am-8:45 am
Nonstop1h 15m
Chicago Midway
Sat 9/19
3:25 pm-5:30 pm
Nonstop1h 05m
$243
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Tue 7/21
7:50 pm-8:05 pm
Nonstop1h 15m
Chicago Midway
Sat 8/1
8:00 am-10:10 am
Nonstop1h 10m
$243
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 8/8
8:54 am-9:17 am
Nonstop1h 23m
Chicago Midway
Mon 8/10
1:25 pm-3:42 pm
Nonstop1h 17m
$252
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 8/8
4:45 pm-4:55 pm
Nonstop1h 10m
Chicago Midway
Mon 8/10
8:15 am-10:30 am
Nonstop1h 15m
$252
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 8/8
4:45 pm-4:55 pm
Nonstop1h 10m
Chicago Midway
Tue 8/11
6:30 am-12:20 pm
1 stop4h 50m
$253
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Thu 8/6
8:55 am-9:15 am
Nonstop1h 20m
Chicago Midway
Mon 8/10
8:15 am-10:30 am
Nonstop1h 15m
$261
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Mon 7/27
6:07 pm-6:25 pm
Nonstop1h 18m
Chicago Midway
Wed 7/29
6:58 pm-9:16 pm
Nonstop1h 18m
$279
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Tue 7/21
3:50 pm-7:35 pm
1 stop4h 45m
Chicago Midway
Thu 7/23
6:50 pm-9:05 pm
Nonstop1h 15m
$289
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Wed 7/22
3:50 pm-9:40 pm
1 stop6h 50m
Chicago Midway
Thu 7/23
7:55 am-10:05 am
Nonstop1h 10m
$289
Cheapest one-way
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Tue 9/15
8:45 am-9:00 am
Nonstop1h 15m
$122
Showing 1-10 of 19 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 June.
| 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 $503). 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 June 23, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 28% 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 June 20, 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 at noon 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 June 23, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 June 23, 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$290 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$98 | Average$301 | FlexibilityNo cancel fee | On-timeN/A |