$69+ Cheap flights from Detroit Metropolitan Wayne County Airport (DTW) to Chicago (CHI)
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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — CHI
Jun 4 — Jun 111
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Detroit to Chicago 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.Cheapflights Tip: The best prices from Detroit Metropolitan Wayne County to Chicago are usually found in September or August, booked 86 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Detroit to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Detroit to ChicagoExplore the most affordable flight options available from Detroit to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Detroit to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/255:43 pm
DTW
- MDW
1 stop18h 29m
Frontier
Mon 6/16:00 am
MDW
- DTW
1 stop17h 39m
Frontier
Deal found 5/3![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/261:59 pm
DTW
- ORD
1 stop18h 56m
Frontier
Thu 5/286:55 am
ORD
- DTW
1 stop16h 43m
Frontier
Deal found 5/4![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 5/4. 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 6/178:10 pm
DTW
- MDW
1 stop4h 00m
Southwest
Wed 6/245:20 pm
MDW
- DTW
1 stop4h 05m
Southwest
Deal found 5/4![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 4/30. 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 5/266:10 am
DTW
- ORD
1 stop7h 40m
Southwest
Wed 5/272:40 pm
ORD
- DTW
1 stop5h 55m
Southwest
Deal found 4/30![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 5/3. 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 5/267:45 pm
DTW
- ORD
Nonstop1h 29m
Delta
Sat 5/301:44 pm
ORD
- DTW
Nonstop1h 26m
Delta
Deal found 5/3![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 5/1. 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 5/266:19 pm
DTW
- MDW
Nonstop1h 14m
Delta
Thu 5/281:22 pm
MDW
- DTW
Nonstop1h 13m
Delta
Deal found 5/1![Delta logo]()
$164
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:45 am
DTW
- ORD
Nonstop1h 45m
American Airlines
Wed 6/246:56 pm
ORD
- DTW
Nonstop1h 38m
American Airlines
Deal found 5/1![American Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:40 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Thu 6/47:00 pm
MDW
- DTW
1 stop4h 15m
Southwest
Deal found 4/30![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 4/30. 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 6/11:00 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Wed 6/310:10 am
MDW
- DTW
2 stops7h 10m
Southwest
Deal found 4/30![Southwest logo]()
$179
This Frontier deal was found by Cheapflights users on 5/3. 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 6/21:59 pm
DTW
- ORD
1 stop6h 30m
Frontier
Wed 6/36:55 am
ORD
- DTW
1 stop9h 18m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 5/3. 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 6/26:50 am
DTW
- MDW
1 stop5h 22m
Frontier
Wed 6/312:04 pm
MDW
- DTW
1 stop11h 35m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 5/3. 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 5/281:59 pm
DTW
- ORD
1 stop6h 42m
Frontier
Mon 6/19:37 pm
ORD
- DTW
1 stop13h 58m
Frontier
Deal found 5/3![Frontier logo]()
$181
Best flights from Detroit to ChicagoDiscover carefully curated flight deals from Detroit to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Detroit to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:19 pm
DTW
- MDW
Nonstop1h 14m
Delta
Thu 6/49:22 am
MDW
- DTW
Nonstop1h 13m
Delta
Deal found 4/30![Delta logo]()
$164
This Southwest deal was found by Cheapflights users on 5/4. 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 6/34:10 pm
DTW
- MDW
1 stop7h 05m
Southwest
Thu 6/41:10 pm
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 5/4![Southwest logo]()
$174
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
DTW
- ORD
Nonstop1h 26m
United Airlines
Mon 6/89:29 pm
ORD
- DTW
Nonstop1h 28m
United Airlines
Deal found 5/4![United Airlines logo]()
$191
This Frontier deal was found by Cheapflights users on 5/4. 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.
Mon 6/151:31 pm
DTW
- ORD
1 stop8h 12m
Frontier
Thu 6/181:29 pm
ORD
- DTW
1 stop10h 15m
Frontier
Deal found 5/4![Frontier logo]()
$270
This KAYAK deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:40 am
DTW
- ORD
Nonstop1h 43m
American Airlines
Fri 5/291:19 pm
ORD
- DTW
1 stop4h 59m
American Airlines
Deal found 4/30![American Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 5/1. 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 6/612:30 pm
DTW
- ORD
Nonstop1h 26m
Delta
Mon 6/87:17 pm
ORD
- DTW
Nonstop1h 33m
Delta
Deal found 5/1![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:25 pm
DTW
- MDW
1 stop5h 30m
Southwest
Mon 6/87:55 am
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 5/1![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 5/2. 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 5/236:19 pm
DTW
- MDW
Nonstop1h 14m
Delta
Mon 5/251:22 pm
MDW
- DTW
Nonstop1h 13m
Delta
Deal found 5/2![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 5/2. 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 5/237:20 am
DTW
- MDW
1 stop8h 55m
Southwest
Mon 5/257:05 pm
MDW
- DTW
Nonstop1h 05m
Southwest
Deal found 5/2![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 5/2. 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 7/110:15 am
DTW
- ORD
Nonstop1h 35m
Delta
Fri 7/311:30 am
ORD
- DTW
Nonstop1h 29m
Delta
Deal found 5/2![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 4/30. 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 5/238:35 am
DTW
- MDW
Nonstop1h 20m
Southwest
Sat 5/2312:45 pm
MDW
- DTW
1 stop7h 45m
Southwest
Deal found 4/30![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 5/287:53 pm
DTW
- RFD
1 stop25h 30m
Multiple Airlines
Mon 6/18:03 pm
RFD
- DTW
1 stop14h 57m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:00 am
DTW
- ORD
Nonstop1h 26m
United Airlines
Wed 7/157:47 pm
ORD
- DTW
Nonstop1h 32m
United Airlines
Deal found 5/1![United Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 4/30. 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 6/51:25 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Tue 6/912:55 pm
MDW
- DTW
Nonstop1h 10m
Southwest
Deal found 4/30![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:07 pm
DTW
- MDW
Nonstop1h 24m
Delta
Mon 7/69:17 am
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/1![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 4/30. 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 5/266:10 am
DTW
- ORD
1 stop7h 40m
Southwest
Tue 5/262:40 pm
ORD
- DTW
1 stop5h 55m
Southwest
Deal found 4/30![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:50 am
DTW
- MDW
Nonstop1h 24m
Delta
Thu 6/111:21 pm
MDW
- DTW
Nonstop1h 18m
Delta
Deal found 5/1![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 5/2. 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 6/64:00 pm
DTW
- ORD
Nonstop1h 29m
Delta
Sat 6/205:22 pm
ORD
- DTW
Nonstop1h 29m
Delta
Deal found 5/2![Delta logo]()
$243
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
DTW
- MDW
1 stop9h 40m
Southwest
Sat 5/309:10 am
MDW
- DTW
1 stop4h 50m
Southwest
Deal found 5/3![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:10 am
DTW
- MDW
2 stops10h 35m
Southwest
Tue 6/93:10 pm
MDW
- DTW
1 stop6h 15m
Southwest
Deal found 5/3![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:00 pm
DTW
- ORD
Nonstop1h 31m
Delta
Wed 7/227:05 am
ORD
- DTW
Nonstop1h 25m
Delta
Deal found 5/3![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Fri 6/198:01 pm
DTW
- RFD
1 stop17h 13m
Multiple Airlines
Mon 6/227:53 pm
RFD
- DTW
2 stops14h 42m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$519
This Southwest deal was found by Cheapflights users on 5/1. 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 5/236:15 am
DTW
- ORD
1 stop10h 15m
Southwest
Sun 5/242:00 pm
ORD
- DTW
1 stop7h 05m
Southwest
Deal found 5/1![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 5/3. 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 5/208:15 am
DTW
- ORD
Nonstop1h 30m
Delta
Wed 5/272:00 pm
ORD
- DTW
Nonstop1h 26m
Delta
Deal found 5/3![Delta logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Thu 5/218:12 pm
DTW
- RFD
1 stop24h 01m
Multiple Airlines
Mon 5/258:03 pm
RFD
- DTW
1 stop14h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$526
This Southwest deal was found by Cheapflights users on 4/30. 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 5/266:10 am
DTW
- ORD
1 stop7h 40m
Southwest
Fri 5/292:40 pm
ORD
- DTW
1 stop6h 40m
Southwest
Deal found 4/30![Southwest logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/232:40 pm
DTW
- RFD
2 stops20h 57m
Multiple Airlines
Mon 5/258:03 pm
RFD
- DTW
1 stop14h 57m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$536
Last-minute flights from Detroit to ChicagoDiscover last-minute flight deals from Detroit to Chicago. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Detroit to Chicago. Data last updated May 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/255:43 pm
DTW
- MDW
1 stop18h 29m
Frontier
Mon 6/16:00 am
MDW
- DTW
1 stop17h 39m
Frontier
Deal found 5/3![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/261:59 pm
DTW
- ORD
1 stop18h 56m
Frontier
Thu 5/286:55 am
ORD
- DTW
1 stop16h 43m
Frontier
Deal found 5/4![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 4/30. 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 5/266:10 am
DTW
- ORD
1 stop7h 40m
Southwest
Wed 5/272:40 pm
ORD
- DTW
1 stop5h 55m
Southwest
Deal found 4/30![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 5/3. 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 5/267:45 pm
DTW
- ORD
Nonstop1h 29m
Delta
Sat 5/301:44 pm
ORD
- DTW
Nonstop1h 26m
Delta
Deal found 5/3![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 5/1. 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 5/266:19 pm
DTW
- MDW
Nonstop1h 14m
Delta
Thu 5/281:22 pm
MDW
- DTW
Nonstop1h 13m
Delta
Deal found 5/1![Delta logo]()
$164
This Frontier deal was found by Cheapflights users on 5/3. 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 5/281:59 pm
DTW
- ORD
1 stop6h 42m
Frontier
Mon 6/19:37 pm
ORD
- DTW
1 stop13h 58m
Frontier
Deal found 5/3![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 4/30. 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 6/11:00 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Wed 6/310:10 am
MDW
- DTW
2 stops7h 10m
Southwest
Deal found 4/30![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:40 pm
DTW
- MDW
Nonstop1h 10m
Southwest
Thu 6/47:00 pm
MDW
- DTW
1 stop4h 15m
Southwest
Deal found 4/30![Southwest logo]()
$174
This Frontier deal was found by Cheapflights users on 5/3. 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 6/21:59 pm
DTW
- ORD
1 stop6h 30m
Frontier
Wed 6/36:55 am
ORD
- DTW
1 stop9h 18m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 5/3. 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 6/26:50 am
DTW
- MDW
1 stop5h 22m
Frontier
Wed 6/312:04 pm
MDW
- DTW
1 stop11h 35m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 5/4. 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 6/178:10 pm
DTW
- MDW
1 stop4h 00m
Southwest
Wed 6/245:20 pm
MDW
- DTW
1 stop4h 05m
Southwest
Deal found 5/4![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:45 am
DTW
- ORD
Nonstop1h 45m
American Airlines
Wed 6/246:56 pm
ORD
- DTW
Nonstop1h 38m
American Airlines
Deal found 5/1![American Airlines logo]()
$172
One-way flights from Detroit to ChicagoSearch for one-way flight options from Detroit to Chicago. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Detroit to Chicago. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Delta deal was found by Cheapflights users on 4/30. 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 5/264:00 pm
DTW
- ORD
Nonstop1h 29m
Delta
Deal found 4/30![Delta logo]()
$69
This Delta deal was found by Cheapflights users on 4/30. 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 5/2612:27 pm
DTW
- MDW
Nonstop1h 15m
Delta
Deal found 4/30![Delta logo]()
$69
This Frontier deal was found by Cheapflights users on 5/3. 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.
Sun 5/241:59 pm
DTW
- ORD
1 stop6h 42m
Frontier
Deal found 5/3![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/21:59 pm
DTW
- MDW
1 stop22h 10m
Frontier
Deal found 5/4![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:20 am
DTW
- MDW
1 stop29h 52m
Frontier
Deal found 5/4![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:59 pm
DTW
- ORD
1 stop6h 30m
Frontier
Deal found 5/1![Frontier logo]()
$76
This Trip.com deal was found by Cheapflights users on 5/3. 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.
Sun 5/241:59 pm
DTW
- MDW
1 stop9h 03m
Frontier
Deal found 5/3![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 5/276:20 am
DTW
- ORD
1 stop14h 21m
Frontier
Deal found 5/4![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 5/276:05 pm
DTW
- MDW
1 stop28h 57m
Frontier
Deal found 5/4![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Fri 5/296:05 pm
DTW
- MDW
1 stop17h 59m
Frontier
Deal found 4/30![Frontier logo]()
$82
This eDestinos deal was found by Cheapflights users on 5/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:10 am
DTW
- ORD
1 stop14h 40m
Frontier
Deal found 5/4![Frontier logo]()
$83
This Southwest deal was found by Cheapflights users on 4/30. 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 5/266:10 am
DTW
- ORD
1 stop7h 40m
Southwest
Deal found 4/30![Southwest logo]()
$84
Find flight deals from Detroit to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $155 (Kiwi.com) |
One-way from | $69 (Delta) |
Popular in | January |
Cheapest in | September |
Average price | $259 |
Good round-trip deal | $394 or less |
Good one-way deal | $162 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Detroit to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
Use the filters below to find and compare flights from Detroit Metropolitan Wayne County Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Tue 6/2
6:19 pm-6:33 pm
Nonstop1h 14m
Chicago Midway
Thu 6/4
9:22 am-11:35 am
Nonstop1h 13m
$164
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Wed 6/3
4:10 pm-10:15 pm
1 stop7h 05m
Chicago Midway
Thu 6/4
1:10 pm-3:20 pm
Nonstop1h 10m
$174
DetroitChicago
DTW - ORD
DTWORD
Detroit Metropolitan Wayne County
Sat 6/6
6:00 am-6:26 am
Nonstop1h 26m
Chicago O'Hare Intl
Mon 6/8
9:29 pm-11:57 pm
Nonstop1h 28m
$191
DetroitChicago
DTW - ORD
DTWORD
Detroit Metropolitan Wayne County
Sat 6/6
12:30 pm-12:56 pm
Nonstop1h 26m
Chicago O'Hare Intl
Mon 6/8
7:17 pm-9:50 pm
Nonstop1h 33m
$191
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 5/23
6:19 pm-6:33 pm
Nonstop1h 14m
Chicago Midway
Mon 5/25
1:22 pm-3:35 pm
Nonstop1h 13m
$191
DetroitChicago
DTW - ORD
DTWORD
Detroit Metropolitan Wayne County
Wed 7/1
10:15 am-10:50 am
Nonstop1h 35m
Chicago O'Hare Intl
Fri 7/3
11:30 am-1:59 pm
Nonstop1h 29m
$196
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 6/6
5:25 pm-9:55 pm
1 stop5h 30m
Chicago Midway
Mon 6/8
7:55 am-10:05 am
Nonstop1h 10m
$201
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 5/23
7:20 am-3:15 pm
1 stop8h 55m
Chicago Midway
Mon 5/25
7:05 pm-9:10 pm
Nonstop1h 05m
$207
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Sat 5/23
8:35 am-8:55 am
Nonstop1h 20m
Chicago Midway
Sat 5/23
12:45 pm-9:30 pm
1 stop7h 45m
$207
Quickest round-trip
DetroitChicago
DTW - MDW
DTWMDW
Detroit Metropolitan Wayne County
Fri 6/5
1:25 pm-1:35 pm
Nonstop1h 10m
Chicago Midway
Tue 6/9
12:55 pm-3:05 pm
Nonstop1h 10m
$216
Showing 1-10 of 56 resultsSorted by cheapest first
Compare providers for flights from Detroit to Chicago
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 Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Detroit Metropolitan Wayne County Airport-Chicago 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Detroit Metropolitan Wayne County Airport-Chicago 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 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Detroit with our price prediction graph.
DTW-CHI
DTW-MDW
DTW-ORD
DTW-RFD
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 Metropolitan Wayne County Airport to Chicago
DTW-CHI
DTW-MDW
DTW-ORD
DTW-RFD
How far ahead should I book a flight from Detroit Metropolitan Wayne County Airport to Chicago?
Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Detroit Metropolitan Wayne County Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Detroit Metropolitan Wayne County Airport to Chicago?
Currently, September is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago (average of $45). Flying from Detroit Metropolitan Wayne County Airport to Chicago in March is currently the most expensive (average of $111). 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 CHI?
Find hourly flight availability from Detroit to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
One of the essential ways to save on airfare from Detroit Metropolitan Wayne County Airport to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 30% on airfare.
What is the cheapest day to fly from Detroit Metropolitan Wayne County Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Detroit to Chicago. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Detroit Metropolitan Wayne County Airport to Chicago 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.
Weekly flight availability from Detroit Metropolitan Wayne County Airport to Chicago
Explore weekly flight availability from Detroit to Chicago. 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 May 5, 2026.
The most flights from DTW to CHI are scheduled on a Monday (106 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (54 on average).
How much does it cost to fly round-trip from Detroit Metropolitan Wayne County Airport to Chicago?
The best insider tips for Detroit Metropolitan Wayne County Airport to Chicago 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 trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 5, 2026.
Read through reviews of airlines operating flights from Detroit Metropolitan Wayne County Airport to Chicago, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Detroit to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Detroit
Popular flights
Alternative routes for Detroit to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Detroit to Chicago by cabin class
Find flights from Detroit to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Detroit and Chicago flights
Browse other Detroit and Chicago flight options. Last updated on May 5, 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 May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Detroit to Chicago
Discover the top 4 airlines that operate flights from Detroit to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$296 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$97 | Average$276 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$97 | Average$317 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$277 | FlexibilityNo cancel fee | On-time71% |