$94+ Cheap flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Oct 22 — Oct 291
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Detroit to Midway
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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 September 22, 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 September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/20. 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 11/46:20 pm -
1 stop4h 15m
Wed 11/118:50 am -
1 stop5h 25m
Deal found 9/20![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:20 am -
2 stops9h 30m
Wed 10/216:00 pm -
Nonstop1h 10m
Deal found 9/21![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:40 pm -
Nonstop1h 20m
Mon 10/269:29 am -
Nonstop1h 14m
Deal found 9/20![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:20 pm -
1 stop4h 10m
Tue 11/101:15 pm -
2 stops7h 55m
Deal found 9/21![Southwest logo]()
$222
This Frontier deal was found by Cheapflights users on 9/20. 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.
Fri 10/237:22 pm -
1 stop5h 21m
Mon 10/261:12 pm -
1 stop7h 32m
Deal found 9/20![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 9/17. 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 10/711:05 am -
1 stop5h 25m
Tue 10/135:30 am -
1 stop6h 00m
Deal found 9/17![Southwest logo]()
$227
This Kissandfly.com deal was found by Cheapflights users on 9/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:28 pm -
Nonstop1h 19m
Mon 10/196:15 am -
1 stop11h 22m
Deal found 9/21![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/228:25 pm -
1 stop3h 45m
Sat 10/242:40 pm -
1 stop6h 20m
Deal found 9/17![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:25 am -
1 stop4h 25m
Mon 10/192:50 pm -
Nonstop1h 05m
Deal found 9/21![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:05 pm -
Nonstop1h 10m
Mon 10/262:50 pm -
Nonstop1h 05m
Deal found 9/21![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:10 am -
Nonstop1h 22m
Tue 10/139:29 am -
Nonstop1h 14m
Deal found 9/18![Delta logo]()
$234
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 September 22, 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 September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:05 pm -
1 stop4h 10m
Wed 10/214:45 pm -
1 stop4h 50m
Deal found 9/21![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:40 pm -
Nonstop1h 20m
Wed 10/211:27 pm -
Nonstop1h 15m
Deal found 9/18![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:05 pm -
Nonstop1h 10m
Mon 10/197:35 pm -
Nonstop1h 10m
Deal found 9/21![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/235:40 pm -
Nonstop1h 20m
Mon 10/269:29 am -
Nonstop1h 14m
Deal found 9/21![Delta logo]()
$221
This Delta deal was found by Cheapflights users on 9/17. 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 10/229:10 am -
Nonstop1h 22m
Fri 10/236:44 pm -
Nonstop1h 14m
Deal found 9/17![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:20 pm -
1 stop4h 10m
Tue 11/101:15 pm -
2 stops7h 55m
Deal found 9/21![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 9/19. 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.
Thu 10/158:10 am -
Nonstop1h 10m
Sat 10/172:40 pm -
1 stop6h 20m
Deal found 9/19![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:40 pm -
Nonstop1h 20m
Mon 10/126:44 pm -
Nonstop1h 14m
Deal found 9/19![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 9/20. 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.
Thu 10/295:25 am -
1 stop5h 35m
Sat 10/318:20 am -
2 stops8h 10m
Deal found 9/20![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:25 pm -
1 stop3h 45m
Fri 10/304:20 pm -
2 stops6h 35m
Deal found 9/21![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/19. 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.
Sat 10/176:20 am -
2 stops9h 30m
Sat 10/246:45 am -
1 stop5h 30m
Deal found 9/19![Southwest logo]()
$252
Last-minute flights from Detroit to MidwayDiscover last-minute flight deals from Detroit to Midway. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Midway. Data last updated September 22, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/711:05 am -
1 stop5h 25m
Tue 10/136:00 pm -
Nonstop1h 10m
Deal found 9/17![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:10 am -
Nonstop1h 22m
Tue 10/139:29 am -
Nonstop1h 14m
Deal found 9/18![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 9/16. 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.
Wed 10/72:25 pm -
Nonstop1h 10m
Fri 10/92:50 pm -
Nonstop1h 05m
Deal found 9/16![Southwest logo]()
$236
This Kissandfly.com deal was found by Cheapflights users on 9/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:28 pm -
Nonstop1h 19m
Mon 10/196:15 am -
1 stop11h 22m
Deal found 9/21![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:25 pm -
1 stop3h 45m
Mon 10/192:50 pm -
Nonstop1h 05m
Deal found 9/21![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 9/19. 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.
Sat 10/176:20 am -
2 stops9h 30m
Sat 10/244:10 pm -
Nonstop1h 10m
Deal found 9/19![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/228:25 pm -
1 stop3h 45m
Sat 10/242:40 pm -
1 stop6h 20m
Deal found 9/17![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:40 pm -
Nonstop1h 20m
Mon 10/269:29 am -
Nonstop1h 14m
Deal found 9/20![Delta logo]()
$221
This Frontier deal was found by Cheapflights users on 9/20. 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.
Fri 10/237:22 pm -
1 stop5h 21m
Mon 10/261:12 pm -
1 stop7h 32m
Deal found 9/20![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 9/19. 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.
Mon 10/268:25 pm -
1 stop3h 45m
Tue 10/272:45 pm -
2 stops6h 00m
Deal found 9/19![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 10/2711:05 am -
2 stops6h 50m
Wed 10/284:45 pm -
1 stop4h 50m
Deal found 9/17![Southwest logo]()
$232
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 September 22, 2026.
Search for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Super.com deal was found by Cheapflights users on 9/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:25 am -
1 stop12h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$94
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:30 pm -
1 stop10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 9/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:02 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$97
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 11/1712:30 pm -
Nonstop1h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$99
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sat 11/146:25 am -
1 stop12h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:03 pm -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:02 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$102
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:53 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$103
This Southwest deal was found by Cheapflights users on 9/16. 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 10/179:15 am -
Nonstop1h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$104
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:00 am -
1 stop11h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 9/18. 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.
Fri 11/133:02 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 9/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:45 pm -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$109
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Southwest) |
One-way from | $94 (Super.com) |
Popular in | February |
Cheapest in | January |
Average price | $367 |
Good round-trip deal | $368 or less |
Good one-way deal | $214 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 7,457,451 searches. Data last updated September 22, 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 Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Tue 11/17
12:30 pm-12:51 pm
Nonstop1h 21m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Thu 11/5
1:30 pm-1:50 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 10/17
5:40 pm-6:00 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
Quickest round-trip
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Wed 10/21
2:25 pm-2:35 pm
Nonstop1h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Tue 10/20
2:25 pm-2:35 pm
Nonstop1h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Thu 11/12
4:50 pm-11:15 pm
1 stop7h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Mon 11/16
5:40 pm-6:04 pm
Nonstop1h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Fri 10/30
9:10 am-9:32 am
Nonstop1h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Mon 10/19
8:05 pm-8:15 pm
Nonstop1h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Tue 10/20
7:05 pm-10:15 pm
1 stop4h 10m
Chicago Midway
Wed 10/21
4:45 pm-10:35 pm
1 stop4h 50m
$217
Showing 1-10 of 20 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 September.
| 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
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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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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 September 22, 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 September 19, 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. Saturday 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 September 22, 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
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
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
Valparaiso
Hammond
Saint Joseph
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 September 22, 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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$372 | FlexibilityNo cancel fee | On-time63% |