$103+ Cheap flights from Denver (DEN) 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Jul 29 — Aug 51
Round-trip
1 adult, Economy
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Find cheap flights from Denver 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.Cheapflights Tip: The best prices from Denver Intl to Chicago Midway are usually found in November or September, booked 54 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Denver to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Denver to MidwayExplore the most affordable flight options available from Denver to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 29, 2026.
Explore the most affordable flight options available from Denver to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 9/21:40 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 9/88:50 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/28![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Thu 8/137:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/25![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/107:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/25![Southwest logo]()
$208
This Frontier deal was found by Cheapflights users on 6/24. 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 8/1110:09 am
DEN
- MDW
1 stop5h 42m
Frontier
Wed 8/124:45 pm
MDW
- DEN
1 stop7h 10m
Frontier
Deal found 6/24![Frontier logo]()
$210
This Southwest deal was found by Cheapflights users on 6/25. 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 8/1211:15 am
DEN
- MDW
1 stop4h 45m
Southwest
Wed 8/192:15 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/25![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:15 am
DEN
- MDW
1 stop5h 40m
Southwest
Sat 7/254:50 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/25![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 8/177:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:00 am
DEN
- MDW
1 stop5h 05m
Southwest
Mon 8/177:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 6/25. 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 7/1812:05 pm
DEN
- MDW
1 stop3h 55m
Southwest
Wed 7/227:40 am
MDW
- DEN
1 stop5h 05m
Southwest
Deal found 6/25![Southwest logo]()
$220
Best flights from Denver to MidwayDiscover carefully curated flight deals from Denver to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 29, 2026.
Discover carefully curated flight deals from Denver to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/118:50 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/26![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:59 am
DEN
- MDW
1 stop7h 14m
Delta
Thu 8/66:42 pm
MDW
- DEN
1 stop5h 06m
Delta
Deal found 6/26![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:30 pm
DEN
- MDW
Nonstop2h 30m
Southwest
Tue 9/18:20 am
MDW
- DEN
1 stop5h 00m
Southwest
Deal found 6/28![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:10 am
DEN
- MDW
1 stop4h 41m
Delta
Tue 12/812:30 pm
MDW
- DEN
1 stop4h 26m
Delta
Deal found 6/25![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:55 pm
DEN
- MDW
1 stop4h 35m
Southwest
Mon 8/315:00 pm
MDW
- DEN
1 stop3h 50m
Southwest
Deal found 6/28![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 6/24. 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 10/25:55 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mon 10/511:45 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 6/24![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 6/28. 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 8/173:15 pm
DEN
- MDW
1 stop3h 30m
Southwest
Fri 8/218:15 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/28![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/27. 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 8/43:56 pm
DEN
- MDW
2 stops25h 05m
Delta
Thu 8/66:42 pm
MDW
- DEN
1 stop5h 06m
Delta
Deal found 6/27![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 6/25. 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 7/238:50 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 7/295:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/25![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sun 7/198:55 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 7/227:40 am
MDW
- DEN
1 stop5h 05m
Southwest
Deal found 6/24![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/28. 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 11/244:45 pm
DEN
- MDW
1 stop5h 05m
Southwest
Mon 11/308:05 am
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/28![Southwest logo]()
$325
Last-minute flights from Denver to MidwayDiscover last-minute flight deals from Denver to Midway. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Denver to Midway. Data last updated June 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/25. 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 7/188:20 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 7/225:30 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/25![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/25. 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 7/1812:05 pm
DEN
- MDW
1 stop3h 55m
Southwest
Tue 7/212:35 pm
MDW
- DEN
1 stop5h 05m
Southwest
Deal found 6/25![Southwest logo]()
$220
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:09 am
DEN
- MDW
1 stop5h 42m
Frontier
Wed 7/224:45 pm
MDW
- DEN
1 stop7h 10m
Frontier
Deal found 6/24![Frontier logo]()
$230
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:15 am
DEN
- MDW
1 stop5h 40m
Southwest
Sat 7/254:50 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/25![Southwest logo]()
$215
This Orbitz deal was found by Cheapflights users on 6/24. 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 7/239:58 am
DEN
- MDW
1 stop11h 05m
Frontier
Tue 7/2812:11 pm
MDW
- DEN
1 stop10h 54m
Frontier
Deal found 6/24![Frontier logo]()
$238
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:59 am
DEN
- MDW
1 stop7h 14m
Delta
Sat 8/11:49 pm
MDW
- DEN
1 stop6h 38m
Delta
Deal found 6/28![Delta logo]()
$225
This Expedia deal was found by Cheapflights users on 6/26. 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.
Sat 7/2511:59 pm
DEN
- MDW
1 stop10h 08m
Frontier
Wed 8/56:05 am
MDW
- DEN
1 stop8h 56m
Frontier
Deal found 6/26![Frontier logo]()
$228
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:40 am
DEN
- MDW
1 stop3h 45m
Southwest
Sat 8/110:15 am
MDW
- DEN
1 stop4h 05m
Southwest
Deal found 6/25![Southwest logo]()
$216
This Trip.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2810:09 am
DEN
- MDW
1 stop5h 42m
Frontier
Tue 8/45:46 pm
MDW
- DEN
1 stop6h 09m
Frontier
Deal found 6/26![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Thu 7/305:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/24![Southwest logo]()
$235
One-way flights from Denver to MidwaySearch for one-way flight options from Denver to Midway. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
Search for one-way flight options from Denver to Midway. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Southwest deal was found by Cheapflights users on 6/25. 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 7/258:20 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/25![Southwest logo]()
$103
This Southwest deal was found by Cheapflights users on 6/26. 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 8/57:25 pm
DEN
- MDW
Nonstop2h 25m
Southwest
Deal found 6/26![Southwest logo]()
$104
This Flightnetwork deal was found by Cheapflights users on 6/24. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 6/24![Frontier logo]()
$105
This Booking.com deal was found by Cheapflights users on 6/28. 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.
Tue 8/411:59 pm
DEN
- MDW
1 stop8h 52m
Frontier
Deal found 6/28![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:40 am
DEN
- MDW
1 stop3h 45m
Southwest
Deal found 6/24![Southwest logo]()
$108
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:15 pm
DEN
- MDW
1 stop3h 30m
Southwest
Deal found 6/25![Southwest logo]()
$109
This Frontier deal was found by Cheapflights users on 6/24. 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 9/2311:59 pm
DEN
- MDW
1 stop9h 59m
Frontier
Deal found 6/24![Frontier logo]()
$111
This Delta deal was found by Cheapflights users on 6/25. 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 7/256:05 am
DEN
- MDW
1 stop5h 33m
Delta
Deal found 6/25![Delta logo]()
$113
This Frontier deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:09 am
DEN
- MDW
1 stop5h 42m
Frontier
Deal found 6/26![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 6/25. 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.
Thu 8/611:46 pm
DEN
- MDW
1 stop9h 05m
Frontier
Deal found 6/25![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 6/24. 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.
Mon 7/2710:09 am
DEN
- MDW
1 stop6h 13m
Frontier
Deal found 6/24![Frontier logo]()
$119
Find flight deals from Denver to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Southwest) |
One-way from | $103 (Southwest) |
Popular in | June |
Cheapest in | November |
Average price | $434 |
Good round-trip deal | $314 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Denver to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 29, 2026.
Use the filters below to find and compare flights from Denver to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 8/8
6:00 am-9:20 am
Nonstop2h 20m
Chicago Midway
Tue 8/11
8:50 pm-10:25 pm
Nonstop2h 35m
$205
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 8/27
6:30 pm-10:00 pm
Nonstop2h 30m
Chicago Midway
Tue 9/1
8:20 am-12:20 pm
1 stop5h 00m
$222
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 7/31
12:59 am-9:13 am
1 stop7h 14m
Chicago Midway
Thu 8/6
6:42 pm-10:48 pm
1 stop5h 06m
$236
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 8/27
3:55 pm-9:30 pm
1 stop4h 35m
Chicago Midway
Mon 8/31
5:00 pm-7:50 pm
1 stop3h 50m
$242
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 10/2
5:55 am-9:15 am
Nonstop2h 20m
Chicago Midway
Mon 10/5
11:45 am-1:25 pm
Nonstop2h 40m
$246
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 8/17
3:15 pm-7:45 pm
1 stop3h 30m
Chicago Midway
Fri 8/21
8:15 pm-9:50 pm
Nonstop2h 35m
$252
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 12/4
6:10 am-11:51 am
1 stop4h 41m
Chicago Midway
Tue 12/8
12:30 pm-3:56 pm
1 stop4h 26m
$255
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 7/23
8:50 pm-12:15 am
Nonstop2h 25m
Chicago Midway
Wed 7/29
5:30 am-7:05 am
Nonstop2h 35m
$265
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sun 7/19
8:55 pm-12:20 am
Nonstop2h 25m
Chicago Midway
Wed 7/22
7:40 am-11:45 am
1 stop5h 05m
$295
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 11/24
4:45 pm-10:50 pm
1 stop5h 05m
Chicago Midway
Mon 11/30
8:05 am-9:55 am
Nonstop2h 50m
$325
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Denver 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 Denver to Midway in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Denver-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 Denver-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Denver-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Denver-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 Denver-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 Denver to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Denver with our price prediction graph.
DEN-MDW
Estimated round-trip price
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Everything you need to know about your flight from Denver to Chicago Midway Airport
How far ahead should I book a flight from Denver to Chicago Midway Airport?
To ensure you get the cheapest price possible for a flight from Denver to Chicago Midway Airport, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Denver to Chicago Midway Airport?
Currently, November is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $218). Flying from Denver to Chicago Midway Airport in June is currently the most expensive (average of $434). 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 DEN to MDW?
Find hourly flight availability from Denver to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 33% on flights from Denver to Chicago Midway Airport by exploring options for tickets in the evening.
What is the cheapest day to fly from Denver to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Denver to Midway. Price data was last updated on June 20, 2026.
Travelers seeking maximum savings on their Denver to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Denver to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 29, 2026.
See what other customers who have flown with Southwest and Frontier from Denver to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Denver 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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 29, 2026.
Denver and Midway flights
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Top 2 airlines flying from Denver to Midway
Discover the top 2 airlines that operate flights from Denver to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$194 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$338 | FlexibilityNo cancel fee | On-time63% |