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Midway

$66+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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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 October 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/412:59 amDEN - MDW
1 stop10h 42mFrontier
Mon 11/1012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 10/20$114
This Frontier deal was found by Cheapflights users on 10/22. 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 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/2112:12 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 10/22$116
This CheapOair deal was found by Cheapflights users on 10/23. 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 12/119:00 pmDEN - MDW
1 stop23h 28mFrontier
Sun 12/1412:18 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 10/23$117
This Priceline deal was found by Cheapflights users on 10/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:42 pmDEN - MDW
1 stop7h 26mFrontier
Mon 11/1712:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 10/23$121
This Frontier deal was found by Cheapflights users on 10/21. 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 11/138:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 10/21$122
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/2210:29 pmDEN - MDW
1 stop10h 50mFrontier
Sun 1/410:50 pmMDW - DEN
Nonstop2h 55mFrontier
Deal found 10/22$123
This Frontier deal was found by Cheapflights users on 10/23. 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 11/98:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/2112:12 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 10/23$125
This Frontier deal was found by Cheapflights users on 10/21. 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 11/171:42 pmDEN - MDW
1 stop7h 29mFrontier
Mon 11/243:31 pmMDW - DEN
Nonstop2h 51mFrontier
Deal found 10/21$126
This Frontier deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:25 pmDEN - MDW
1 stop8h 10mFrontier
Fri 11/2112:12 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 10/23$130
This Priceline deal was found by Cheapflights users on 10/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 10/23$131
This Frontier deal was found by Cheapflights users on 10/20. 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 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Sat 11/156:15 amMDW - DEN
1 stop14h 44mFrontier
Deal found 10/20$132
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Sun 12/216:27 pmDEN - MDW
Nonstop2h 23mFrontier
Wed 12/248:15 amMDW - DEN
1 stop14h 53mFrontier
Deal found 10/22$133

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$114
(Kiwi.com)

One-way from

$66
(Priceline)

Popular in

November

Cheapest in

September

Average price

$425
Provider with most accurate pricing for Jackson Hole-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson Hole-Chicago (CHI) flights.
Search Deals
From Wyoming to Chicago Midway
Search Deals
One-way flight from Wyoming to Chicago Midway
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($169 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 23, 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

Sat 12/20

6:35 pm-9:55 pm

Nonstop2h 20m

Chicago Midway

Wed 12/24

7:05 am-8:45 am

Nonstop2h 40m

$187

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

10:30 am-6:34 pm

1 stop7h 04m

Chicago Midway

Mon 1/19

5:25 pm-11:54 pm

1 stop7h 29m

$197

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 11/11

4:44 pm-11:40 pm

1 stop5h 56m

Chicago Midway

Tue 11/18

9:34 am-2:15 pm

1 stop5h 41m

$199

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 12/13

4:44 pm-11:47 pm

1 stop6h 03m

Chicago Midway

Sun 12/14

5:13 pm-10:53 pm

1 stop6h 40m

$199

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 11/11

6:15 am-12:34 pm

1 stop5h 19m

Chicago Midway

Sat 11/15

9:32 am-2:15 pm

1 stop5h 43m

$199

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 10/31

2:10 pm-7:10 pm

1 stop4h 00m

Chicago Midway

Tue 11/4

8:10 am-12:10 pm

1 stop5h 00m

$207

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 11/12

9:40 am-1:00 pm

Nonstop2h 20m

Chicago Midway

Fri 11/21

7:45 am-9:25 am

Nonstop2h 40m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 12/18

1:00 pm-6:30 pm

1 stop4h 30m

Chicago Midway

Sun 12/21

5:50 pm-9:50 pm

1 stop5h 00m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 11/19

12:40 pm-3:55 pm

Nonstop2h 15m

Chicago Midway

Wed 11/26

10:30 pm-12:10 am

Nonstop2h 40m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 11/8

1:50 pm-8:35 pm

1 stop5h 45m

Chicago Midway

Wed 11/12

2:35 pm-4:15 pm

Nonstop2h 40m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 54 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 2h 20m. 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.

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
Porter
Benton Harbor

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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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