$92+ Cheap flights from Detroit (DTT) 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
Nov 8 — Nov 151
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 October 9, 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 October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/8. 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 stop4h 25m
Mon 11/23:05 pm -
Nonstop1h 10m
Deal found 10/8![Southwest logo]()
$217
This Frontier deal was found by Cheapflights users on 10/7. 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 10/267:25 pm -
1 stop5h 18m
Thu 10/2912:20 pm -
1 stop8h 23m
Deal found 10/7![Frontier logo]()
$218
This Delta deal was found by Cheapflights users on 10/5. 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 10/315:40 pm -
Nonstop1h 20m
Mon 11/26:44 pm -
Nonstop1h 14m
Deal found 10/5![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 10/4. 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 11/42:15 pm -
Nonstop1h 20m
Thu 11/56:50 pm -
Nonstop1h 15m
Deal found 10/4![Southwest logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/72:51 pm -
1 stop9h 56m
Mon 11/96:42 pm -
2 stops15h 58m
Deal found 10/8![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 10/5. 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 10/289:00 am -
Nonstop1h 10m
Sat 10/318:20 am -
2 stops8h 10m
Deal found 10/5![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/5. 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 11/48:50 am -
Nonstop1h 20m
Wed 11/111:15 pm -
2 stops7h 55m
Deal found 10/5![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 10/8. 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 11/189:10 am -
Nonstop1h 36m
Sun 11/226:44 pm -
Nonstop1h 16m
Deal found 10/8![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 10/4. 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 11/74:45 pm -
Nonstop1h 20m
Mon 11/96:50 pm -
Nonstop1h 15m
Deal found 10/4![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 10/7. 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
Thu 10/292:50 pm -
Nonstop1h 05m
Deal found 10/7![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 10/6. 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 11/129:10 am -
Nonstop1h 36m
Mon 11/161:31 pm -
Nonstop1h 13m
Deal found 10/6![Delta logo]()
$231
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 October 9, 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 October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/8. 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 12/158:50 am -
Nonstop1h 20m
Sat 12/197:40 am -
Nonstop1h 10m
Deal found 10/8![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 10/7. 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 10/2912:28 pm -
Nonstop1h 19m
Fri 10/301:27 pm -
Nonstop1h 15m
Deal found 10/7![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 10/5. 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 10/284:10 pm -
1 stop6h 15m
Sat 10/318:20 am -
2 stops8h 10m
Deal found 10/5![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 10/8. 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 11/98:45 pm -
1 stop4h 25m
Tue 11/101:15 pm -
2 stops7h 55m
Deal found 10/8![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 10/5. 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 11/101:25 pm -
1 stop6h 40m
Wed 11/111:15 pm -
2 stops7h 55m
Deal found 10/5![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 10/5. 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 11/111:25 pm -
1 stop3h 50m
Sat 11/147:35 am -
1 stop4h 25m
Deal found 10/5![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 10/5. 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 11/27:45 pm -
Nonstop1h 20m
Mon 11/96:50 pm -
Nonstop1h 15m
Deal found 10/5![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/5. 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 11/191:25 pm -
1 stop6h 40m
Thu 11/267:55 am -
Nonstop1h 15m
Deal found 10/5![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 10/6. 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 10/298:10 am -
Nonstop1h 10m
Fri 10/308:35 am -
1 stop6h 45m
Deal found 10/6![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/8. 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 11/138:15 pm -
1 stop3h 30m
Mon 11/161:15 pm -
2 stops7h 55m
Deal found 10/8![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 10/7. 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 10/298:25 pm -
1 stop3h 45m
Mon 11/212:45 pm -
2 stops5h 50m
Deal found 10/7![Southwest logo]()
$288
Last-minute flights from Detroit to MidwayDiscover last-minute flight deals from Detroit to Midway. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Midway. Data last updated October 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 10/7. 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 10/267:25 pm -
1 stop5h 18m
Thu 10/2912:20 pm -
1 stop8h 23m
Deal found 10/7![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 10/7. 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
Thu 10/292:50 pm -
Nonstop1h 05m
Deal found 10/7![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 10/5. 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 10/289:00 am -
Nonstop1h 10m
Sat 10/318:20 am -
2 stops8h 10m
Deal found 10/5![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/8. 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 stop4h 25m
Mon 11/23:05 pm -
Nonstop1h 10m
Deal found 10/8![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 10/5. 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 10/315:40 pm -
Nonstop1h 20m
Mon 11/26:44 pm -
Nonstop1h 14m
Deal found 10/5![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 10/4. 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 11/42:15 pm -
Nonstop1h 20m
Thu 11/56:50 pm -
Nonstop1h 15m
Deal found 10/4![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 10/5. 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 11/48:50 am -
Nonstop1h 20m
Wed 11/111:15 pm -
2 stops7h 55m
Deal found 10/5![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/72:51 pm -
1 stop9h 56m
Mon 11/96:42 pm -
2 stops15h 58m
Deal found 10/8![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 10/5. 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 11/74:45 pm -
Nonstop1h 20m
Mon 11/96:50 pm -
Nonstop1h 15m
Deal found 10/5![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/6. 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 11/129:10 am -
Nonstop1h 36m
Mon 11/161:31 pm -
Nonstop1h 13m
Deal found 10/6![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/8. 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 11/189:10 am -
Nonstop1h 36m
Sun 11/226:44 pm -
Nonstop1h 16m
Deal found 10/8![Delta 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 October 9, 2026.
Search for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Frontier deal was found by Cheapflights users on 10/8. 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 10/8![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 10/5. 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 11/72:51 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$94
This Mytrip deal was found by Cheapflights users on 10/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:02 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 10/6. 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 10/316:25 am -
1 stop12h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 10/6. 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.
Thu 10/296:41 am -
1 stop12h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 10/8. 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.
Tue 11/36:25 am -
1 stop12h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$102
This Southwest deal was found by Cheapflights users on 10/7. 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 11/37:35 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 12/82:31 pm -
1 stop19h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$107
Find flight deals from Detroit to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTT) 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 October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Southwest) |
One-way from | $92 (Frontier) |
Popular in | October |
Cheapest in | February |
Average price | $712 |
Good round-trip deal | $367 or less |
Good one-way deal | $217 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 October 9, 2026.
Use the filters below to find and compare flights from Detroit 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
Thu 11/5
9:10 am-9:32 am
Nonstop1h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
Quickest round-trip
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Thu 10/29
8:10 am-8:20 am
Nonstop1h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 10/31
12:28 pm-12:47 pm
Nonstop1h 19m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Thu 10/29
12:28 pm-12:47 pm
Nonstop1h 19m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Thu 12/10
5:30 am-9:00 am
1 stop4h 30m
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
Sun 11/22
5:40 pm-6:04 pm
Nonstop1h 24m
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
Thu 11/19
6:20 pm-9:35 pm
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$126
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Fri 11/6
7:45 pm-8:05 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sun 12/27
8:00 pm-8:20 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Tue 12/1
12:44 pm-1:01 pm
Nonstop1h 17m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
Showing 1-10 of 22 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Detroit-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-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Detroit-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Detroit-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-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.
DTT-MDW
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.
Cheapflights Insights
Everything you need to know about your flight from Detroit to Chicago Midway Airport
DTT-MDW
DTW-MDW
What is the cheapest month to book a flight from Detroit to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Detroit to Chicago Midway Airport (average of $171). Flying from Detroit to Chicago Midway Airport in September is currently the most expensive (average of $442). 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 DTT 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 October 9, 2026.
A simple way to save on the total cost of your ticket is to fly from Detroit to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.
Weekly flight availability from Detroit to Chicago Midway Airport
Explore weekly flight availability from Detroit to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 9, 2026.
The most flights from DTT to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).
What is the cheapest day to fly from Detroit 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 October 3, 2026.
Travelers seeking maximum savings on their Detroit to Chicago Midway Airport flight should consider departing on Friday 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.
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 October 9, 2026.
Read reviews from past customers who have flown Southwest from Detroit to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
7.9
Food
7.0
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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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 October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$362 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$372 | FlexibilityNo cancel fee | On-time63% |