$99+ Cheap flights from Denver (DEN) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Dec 10 — Dec 171
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 December or April, booked 72 days in advance, depart on a Friday or Thursday and return on a Wednesday
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 November 10, 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 November 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:46 pm -
1 stop11h 59m
Tue 12/812:28 pm -
1 stop8h 29m
Deal found 11/5![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:41 am -
1 stop9h 35m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:40 pm -
1 stop12h 05m
Sat 12/198:35 pm -
1 stop14h 14m
Deal found 11/5![Frontier logo]()
$197
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:41 am -
1 stop9h 35m
Wed 12/910:40 am -
1 stop6h 03m
Deal found 11/5![Frontier logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:59 pm -
1 stop13h 42m
Wed 12/910:40 am -
1 stop12h 15m
Deal found 11/7![Frontier logo]()
$202
This Expedia deal was found by Cheapflights users on 11/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/169:00 am -
1 stop11h 02m
Thu 12/178:35 pm -
1 stop26h 13m
Deal found 11/5![Frontier logo]()
$204
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:00 am -
1 stop6h 07m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$205
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:59 pm -
1 stop18h 43m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:59 pm -
1 stop18h 43m
Tue 12/1512:28 pm -
1 stop8h 29m
Deal found 11/7![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:05 am -
Nonstop2h 25m
Tue 12/1510:50 am -
Nonstop2h 40m
Deal found 11/8![Southwest logo]()
$209
This Frontier deal was found by Cheapflights users on 11/7. 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 12/18:46 pm -
1 stop11h 40m
Tue 12/812:28 pm -
1 stop8h 29m
Deal found 11/7![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:46 pm -
1 stop11h 59m
Sun 12/68:37 pm -
1 stop14h 12m
Deal found 11/5![Frontier logo]()
$211
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 November 10, 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 November 10, 2026.
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:55 am -
1 stop5h 00m
Thu 12/105:00 pm -
1 stop6h 05m
Deal found 11/5![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:13 am -
1 stop4h 37m
Thu 12/1010:24 am -
1 stop6h 38m
Deal found 11/8![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 11/6. 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.
Wed 1/611:25 am -
1 stop3h 55m
Sat 1/96:30 am -
Nonstop2h 45m
Deal found 11/6![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:55 pm -
Nonstop2h 20m
Tue 12/2210:50 pm -
Nonstop2h 50m
Deal found 11/9![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 11/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2812:55 am -
1 stop6h 54m
Sat 1/26:30 pm -
1 stop5h 45m
Deal found 11/9![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/128:45 pm -
Nonstop2h 25m
Tue 2/167:50 pm -
Nonstop2h 45m
Deal found 11/9![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 11/7. 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.
Wed 12/911:05 am -
1 stop5h 00m
Sat 12/1211:05 am -
2 stops7h 35m
Deal found 11/7![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:05 pm -
Nonstop2h 25m
Sun 1/36:00 am -
Nonstop2h 45m
Deal found 11/5![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1411:25 am -
1 stop3h 55m
Sun 1/176:15 am -
Nonstop2h 45m
Deal found 11/9![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:05 pm -
Nonstop2h 20m
Sun 12/69:25 pm -
Nonstop2h 50m
Deal found 11/9![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:05 am -
Nonstop2h 25m
Sun 12/69:25 pm -
Nonstop2h 50m
Deal found 11/9![Southwest logo]()
$350
Last-minute flights from Denver to MidwayDiscover last-minute flight deals from Denver to Midway. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Denver to Midway. Data last updated November 10, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/7. 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 12/18:46 pm -
1 stop11h 40m
Tue 12/812:28 pm -
1 stop8h 29m
Deal found 11/7![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:59 pm -
1 stop13h 42m
Wed 12/910:40 am -
1 stop12h 15m
Deal found 11/7![Frontier logo]()
$202
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:00 am -
1 stop6h 07m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:46 pm -
1 stop11h 59m
Tue 12/812:28 pm -
1 stop8h 29m
Deal found 11/5![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:46 pm -
1 stop11h 59m
Sun 12/68:37 pm -
1 stop14h 12m
Deal found 11/5![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:41 am -
1 stop9h 35m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$194
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:41 am -
1 stop9h 35m
Wed 12/910:40 am -
1 stop6h 03m
Deal found 11/5![Frontier logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:40 pm -
1 stop12h 05m
Sat 12/198:35 pm -
1 stop14h 14m
Deal found 11/5![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:05 am -
Nonstop2h 25m
Tue 12/1510:50 am -
Nonstop2h 40m
Deal found 11/8![Southwest logo]()
$209
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:59 pm -
1 stop18h 43m
Sat 12/1210:40 am -
1 stop12h 15m
Deal found 11/5![Frontier logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:59 pm -
1 stop18h 43m
Tue 12/1512:28 pm -
1 stop8h 29m
Deal found 11/7![Frontier logo]()
$208
This Expedia deal was found by Cheapflights users on 11/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/169:00 am -
1 stop11h 02m
Thu 12/178:35 pm -
1 stop26h 13m
Deal found 11/5![Frontier logo]()
$204
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 November 10, 2026.
Search for one-way flight options from Denver to Midway. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Expedia deal was found by Cheapflights users on 11/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:40 pm -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/310:41 am -
1 stop8h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 11/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:40 pm -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:30 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2111:30 pm -
1 stop19h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/129:35 am -
1 stop6h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2410:59 am -
1 stop12h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 11/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:46 pm -
1 stop11h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 11/9. 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 1/59:37 pm -
1 stop9h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$111
This CheapOair deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/611:11 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$112
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $192 (Cheapflightsfares) |
One-way from | $99 (Expedia) |
Popular in | June |
Cheapest in | December |
Average price | $345 |
Good round-trip deal | $319 or less |
Good one-way deal | $214 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 7,457,451 searches. Data last updated November 10, 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
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 12/15
6:05 pm-9:30 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Wed 1/6
11:10 am-4:45 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$127
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 12/22
8:55 pm-12:15 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 2/23
6:50 am-10:15 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 12/19
9:30 pm-12:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Tue 12/1
6:05 pm-9:30 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 12/21
12:55 am-8:49 am
1 stop6h 54m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 2/22
6:20 am-9:45 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 12/7
7:05 am-10:30 am
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Mon 1/4
6:20 am-12:04 pm
1 stop4h 44m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| 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
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 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 71 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, December is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $241). 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 November 10, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 24% on flights from Denver to Chicago Midway Airport by exploring options for tickets in the afternoon.
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 November 7, 2026.
Travelers seeking maximum savings on their Denver to Chicago Midway Airport flight should consider departing on Tuesday 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 November 10, 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Entertainment
7.4
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
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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 7,457,451 searches. Data last updated November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$364 | FlexibilityNo cancel fee | On-time63% |