$110+ Cheap flights from Detroit (DTT) 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
Sep 8 — Sep 151
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 August 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 August 9, 2026.
This Frontier deal was found by Cheapflights users on 8/6. 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.
Sat 10/37:00 am -
1 stop11h 51m
Sun 10/412:54 pm -
1 stop7h 38m
Deal found 8/6![Frontier logo]()
$198
This Travelocity deal was found by Cheapflights users on 8/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:50 am -
1 stop5h 08m
Tue 10/1312:03 pm -
1 stop11h 39m
Deal found 8/8![Frontier logo]()
$200
This Frontier deal was found by Cheapflights users on 8/6. 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.
Tue 8/256:00 am -
1 stop5h 55m
Thu 8/279:26 pm -
1 stop12h 46m
Deal found 8/6![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 8/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:25 pm -
1 stop9h 19m
Mon 10/512:54 pm -
1 stop7h 38m
Deal found 8/4![Frontier logo]()
$207
This Orbitz deal was found by Cheapflights users on 8/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:38 pm -
1 stop7h 20m
Fri 10/236:40 am -
1 stop7h 03m
Deal found 8/6![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am -
1 stop11h 51m
Mon 9/286:25 am -
2 stops27h 18m
Deal found 8/6![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am -
1 stop11h 46m
Thu 9/1712:54 pm -
1 stop7h 38m
Deal found 8/9![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
1 stop11h 51m
Wed 9/236:25 am -
2 stops10h 24m
Deal found 8/6![Frontier logo]()
$216
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 9/54:45 pm -
Nonstop1h 10m
Sun 9/66:25 pm -
Nonstop1h 10m
Deal found 8/7![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 8/5. 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 9/58:54 am -
Nonstop1h 23m
Sun 9/69:24 am -
Nonstop1h 16m
Deal found 8/5![Delta logo]()
$218
This Frontier deal was found by Cheapflights users on 8/9. 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 10/23:25 pm -
1 stop9h 19m
Sun 10/412:54 pm -
1 stop7h 38m
Deal found 8/9![Frontier logo]()
$226
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 August 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 August 9, 2026.
This Delta deal was found by Cheapflights users on 8/5. 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 9/58:54 am -
Nonstop1h 23m
Sun 9/69:24 am -
Nonstop1h 16m
Deal found 8/5![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/111:20 pm -
Nonstop1h 10m
Tue 9/153:05 pm -
1 stop5h 15m
Deal found 8/6![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 9/68:54 am -
Nonstop1h 23m
Thu 9/105:37 pm -
Nonstop1h 16m
Deal found 8/7![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 9/198:30 am -
Nonstop1h 15m
Thu 9/247:55 am -
1 stop3h 45m
Deal found 8/6![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 8/5. 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 10/36:05 pm -
Nonstop1h 17m
Mon 10/57:01 pm -
Nonstop1h 19m
Deal found 8/5![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/7. 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.
Fri 8/281:20 pm -
Nonstop1h 10m
Tue 9/88:35 am -
Nonstop1h 20m
Deal found 8/7![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 8/6. 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.
Sat 9/198:45 am -
Nonstop1h 22m
Thu 9/247:01 pm -
Nonstop1h 19m
Deal found 8/6![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/5. 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 10/198:25 pm -
1 stop3h 40m
Thu 10/226:25 pm -
1 stop4h 30m
Deal found 8/5![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/8. 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.
Wed 9/912:55 pm -
Nonstop1h 10m
Fri 9/115:30 pm -
1 stop4h 10m
Deal found 8/8![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Sun 9/61:45 pm -
2 stops8h 25m
Deal found 8/7![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/8. 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.
Wed 10/1411:05 am -
1 stop5h 25m
Sun 10/187:45 am -
Nonstop1h 10m
Deal found 8/8![Southwest logo]()
$315
Last-minute flights from Detroit to MidwayDiscover last-minute flight deals from Detroit to Midway. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Midway. Data last updated August 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/6. 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.
Tue 8/256:00 am -
1 stop5h 55m
Thu 8/279:26 pm -
1 stop12h 46m
Deal found 8/6![Frontier logo]()
$205
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/31:35 pm -
Nonstop1h 10m
Sun 9/68:50 am -
Nonstop1h 15m
Deal found 8/4![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 9/54:45 pm -
Nonstop1h 10m
Sun 9/66:25 pm -
Nonstop1h 10m
Deal found 8/7![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 8/5. 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 9/58:54 am -
Nonstop1h 23m
Sun 9/69:24 am -
Nonstop1h 16m
Deal found 8/5![Delta logo]()
$218
This Frontier deal was found by Cheapflights users on 8/7. 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.
Tue 9/86:00 am -
1 stop5h 55m
Thu 9/1012:54 pm -
1 stop7h 38m
Deal found 8/7![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 8/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am -
1 stop11h 51m
Fri 9/2512:54 pm -
1 stop7h 38m
Deal found 8/4![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
1 stop11h 51m
Wed 9/236:25 am -
2 stops10h 24m
Deal found 8/6![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am -
1 stop11h 51m
Mon 9/286:25 am -
2 stops27h 18m
Deal found 8/6![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 8/9. 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 9/237:00 am -
1 stop11h 51m
Fri 9/2512:54 pm -
1 stop7h 38m
Deal found 8/9![Frontier logo]()
$213
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 August 9, 2026.
Search for one-way flight options from Detroit to Midway. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Frontier deal was found by Cheapflights users on 8/7. 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.
Fri 8/2812:07 pm -
1 stop9h 24m
Deal found 8/7![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Mon 11/26:50 am -
1 stop5h 08m
Deal found 8/8![Frontier logo]()
$112
This Expedia deal was found by Cheapflights users on 8/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:38 pm -
1 stop7h 20m
Deal found 8/4![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/154:23 pm -
2 stops26h 28m
Deal found 8/8![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:23 pm -
2 stops26h 28m
Deal found 8/4![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 11/76:50 am -
1 stop5h 08m
Deal found 8/9![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/294:23 pm -
2 stops26h 28m
Deal found 8/7![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am -
1 stop5h 55m
Deal found 8/8![Frontier logo]()
$118
This Booking.com deal was found by Cheapflights users on 8/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am -
1 stop11h 46m
Deal found 8/4![Frontier logo]()
$119
This Expedia deal was found by Cheapflights users on 8/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:00 am -
1 stop6h 59m
Deal found 8/7![Frontier logo]()
$120
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 August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Frontier) |
One-way from | $110 (Frontier) |
Popular in | October |
Cheapest in | September |
Average price | $410 |
Good round-trip deal | $366 or less |
Good one-way deal | $202 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 August 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
Sat 9/5
8:54 am-9:17 am
Nonstop1h 23m
Chicago Midway
Sun 9/6
9:24 am-11:40 am
Nonstop1h 16m
$218
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sun 9/6
8:54 am-9:17 am
Nonstop1h 23m
Chicago Midway
Thu 9/10
5:37 pm-7:53 pm
Nonstop1h 16m
$233
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Fri 9/11
1:20 pm-1:30 pm
Nonstop1h 10m
Chicago Midway
Tue 9/15
3:05 pm-9:20 pm
1 stop5h 15m
$243
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 10/3
6:05 pm-6:22 pm
Nonstop1h 17m
Chicago Midway
Mon 10/5
7:01 pm-9:20 pm
Nonstop1h 19m
$249
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 9/19
8:45 am-9:07 am
Nonstop1h 22m
Chicago Midway
Thu 9/24
7:01 pm-9:20 pm
Nonstop1h 19m
$249
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 9/19
8:30 am-8:45 am
Nonstop1h 15m
Chicago Midway
Thu 9/24
7:55 am-12:40 pm
1 stop3h 45m
$259
Quickest round-trip
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Fri 8/28
1:20 pm-1:30 pm
Nonstop1h 10m
Chicago Midway
Tue 9/8
8:35 am-10:55 am
Nonstop1h 20m
$268
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Mon 10/19
8:25 pm-11:05 pm
1 stop3h 40m
Chicago Midway
Thu 10/22
6:25 pm-11:55 pm
1 stop4h 30m
$269
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Wed 9/9
12:55 pm-1:05 pm
Nonstop1h 10m
Chicago Midway
Fri 9/11
5:30 pm-10:40 pm
1 stop4h 10m
$291
DetroitChicago
DTW Detroit Metropolitan Wayne County - MDW Chicago Midway
DTWMDW
Detroit Metropolitan Wayne County
Sat 9/5
2:50 pm-8:35 pm
1 stop6h 45m
Chicago Midway
Sun 9/6
1:45 pm-11:10 pm
2 stops8h 25m
$296
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 August.
| 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 February is currently the most expensive (average of $435). 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 August 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 30% on your trip compared to booking a flight at noon.
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 August 9, 2026.
The most flights from DTT to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, 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 August 1, 2026.
Travelers seeking maximum savings on their Detroit to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 9, 2026.
Read reviews from past customers who have flown Southwest and Delta 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from Detroit
Popular flights
Alternative routes for Detroit to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Detroit to Midway by cabin class
Find flights from Detroit to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 August 9, 2026.
Detroit and Midway flights
Browse other Detroit and Midway flight options. Last updated on August 9, 2026.
Other flights from Detroit
Browse through other flights departing from Detroit. Flights are based on user searches made on Cheapflights and were last updated on August 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$341 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$121 | Average$325 | FlexibilityNo cancel fee | On-timeN/A |