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$63+ Cheap flights from Wyoming 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Wyoming to Midway

Keep the following information in mind while searching for Wyoming to Midway flight deals. Data was last updated September 15, 2025.

Round-trip from

$116
(CheapOair)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$289
From Wyoming to Chicago Midway
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One-way flight from Wyoming to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Wyoming to Midway

Cheapest flights from Wyoming to Midway
Explore the most affordable flight options available from Wyoming to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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.
Mon 10/277:49 amDEN - MDW
Nonstop2h 27mFrontier
Fri 10/311:37 pmMDW - DEN
1 stop8h 53mFrontier
Deal found 9/13$116
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/14$117
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/1612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$119
This CheapOair deal was found by Cheapflights users on 9/14. 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 11/78:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$120
This Frontier deal was found by Cheapflights users on 9/13. 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 10/2212:36 amDEN - MDW
1 stop8h 11mFrontier
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/13$122
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/136:05 amDEN - MDW
Nonstop2h 26mFrontier
Fri 10/175:20 pmMDW - DEN
1 stop6h 39mFrontier
Deal found 9/15$124
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Wed 11/512:16 amDEN - MDW
1 stop7h 56mFrontier
Mon 11/1012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$125
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:05 amDEN - MDW
Nonstop2h 25mFrontier
Mon 11/1012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/13$128
This CheapOair deal was found by Cheapflights users on 9/13. 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 10/108:58 pmDEN - MDW
Nonstop2h 26mFrontier
Sun 10/125:20 amMDW - DEN
1 stop20h 31mFrontier
Deal found 9/13$129
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:12 pmDEN - MDW
Nonstop2h 24mFrontier
Sun 10/195:20 amMDW - DEN
1 stop28h 23mFrontier
Deal found 9/13$130
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:58 pmSLC - MDW
1 stop13h 15mFrontier
Mon 10/1310:56 pmMDW - SLC
1 stop12h 32mFrontier
Deal found 9/14$171
This CheapOair deal was found by Cheapflights users on 9/13. 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 10/248:59 pmSLC - MDW
1 stop25h 21mFrontier
Mon 10/2712:11 pmMDW - SLC
1 stop24h 29mFrontier
Deal found 9/13$172

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wyoming 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 September 15, 2025.
Use the filters below to find and compare flights from Wyoming to Chicago Midway Airport that are best for you.

Fly from

Wyoming

Fly to

Midway

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 11/4

10:15 am-5:15 pm

1 stop6h 00m

Chicago Midway

Thu 11/6

9:40 pm-11:15 pm

Nonstop2h 35m

$152

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

Mon 10/20

9:50 pm-11:25 pm

Nonstop2h 35m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 10/7

1:30 pm-7:25 pm

1 stop4h 55m

Chicago Midway

Sat 10/11

12:20 pm-2:00 pm

Nonstop2h 40m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 10/7

7:55 am-12:40 pm

1 stop3h 45m

Chicago Midway

Tue 10/7

8:40 pm-10:20 pm

Nonstop2h 40m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 11/13

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Sun 11/16

7:45 am-9:25 am

Nonstop2h 40m

$177

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/25

5:25 pm-8:45 pm

Nonstop2h 20m

Chicago Midway

Sun 10/26

7:45 am-9:25 am

Nonstop2h 40m

$177

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/14

4:40 pm-8:00 pm

Nonstop2h 20m

Chicago Midway

Fri 2/20

3:45 pm-9:10 pm

1 stop6h 25m

$178

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 12/23

8:20 pm-11:40 pm

Nonstop2h 20m

Chicago Midway

Thu 12/25

7:05 am-8:45 am

Nonstop2h 40m

$179

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 10/29

1:40 pm-5:00 pm

Nonstop2h 20m

Chicago Midway

Sun 11/2

5:15 am-6:55 am

Nonstop2h 40m

$187

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Fri 12/12

12:42 pm-8:36 pm

1 stop6h 54m

Chicago Midway

Thu 12/18

1:35 pm-12:08 am

1 stop11h 33m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 50 results
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Best time to book a flight from Wyoming to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Wyoming with our price prediction graph.
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 Wyoming to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Wyoming to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wyoming to Chicago Midway Airport?

    Departing from Wyoming to Chicago Midway Airport will take you 6h. There are 893 mi between Wyoming and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the most popular routes from Wyoming to Chicago Midway Airport?

    When deciding which route to take from Wyoming to Chicago Midway Airport consider Denver Intl - Chicago Midway, Salt Lake City - Chicago Midway or Jackson Hole - Chicago Midway as they are the most popular.

  • Can I find deals for flights from Wyoming to Midway that include hotel bookings?

    Yes. In addition to deals on Wyoming to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wyoming to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wyoming to Midway.

  • Can I find deals for business class flights from Wyoming to Midway?

    Yes. Cheapflights offers flight deals from Wyoming to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wyoming to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Wyoming to Chicago Midway Airport (average of $160). Flying from Wyoming to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Wyoming to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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