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$69+ Cheap flights from Midway (MDW) to Wyoming

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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAC
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
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Cheap flight deals from Midway to Wyoming

Keep the following information in mind while searching for Midway to Wyoming flight deals. Data was last updated January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(Frontier)

One-way from

$69
(Trip.com)

Popular in

November

Cheapest in

October

Average price

$457
Provider with most accurate pricing for Chicago (CHI)-Jackson Hole flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson Hole flights.
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From Chicago Midway to Wyoming
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One-way flight from Chicago Midway to Wyoming
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Highest demand for flights based on searches. 6% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Midway to Wyoming

Cheapest flights from Midway to Wyoming
Explore the most affordable flight options available from Midway to Wyoming. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 7, 2026.

This Frontier deal was found by Cheapflights users on 1/7. 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.
Sat 2/219:15 amMDW - DEN
1 stop12h 18mFrontier
Sat 2/281:42 pmDEN - MDW
1 stop6h 57mFrontier
Deal found 1/7$128
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:15 amMDW - DEN
1 stop13h 20mFrontier
Thu 3/512:42 pmDEN - MDW
1 stop7h 30mFrontier
Deal found 1/7$130
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/239:45 amMDW - DEN
1 stop6h 31mFrontier
Mon 1/266:30 amDEN - MDW
1 stop8h 19mFrontier
Deal found 1/7$133
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/269:45 amMDW - DEN
1 stop6h 31mFrontier
Thu 2/510:29 pmDEN - MDW
1 stop16h 29mFrontier
Deal found 1/5$135
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:16 pmMDW - DEN
1 stop7h 24mFrontier
Thu 4/26:30 amDEN - MDW
1 stop6h 29mFrontier
Deal found 1/6$140
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/199:09 pmMDW - DEN
Nonstop2h 50mFrontier
Mon 1/266:30 amDEN - MDW
1 stop8h 19mFrontier
Deal found 1/5$142
This Southwest deal was found by Cheapflights users on 1/6. 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.
Tue 2/32:10 pmMDW - DEN
Nonstop2h 40mSouthwest
Tue 2/106:25 pmDEN - MDW
Nonstop2h 25mSouthwest
Deal found 1/6$143
This Frontier deal was found by Cheapflights users on 1/7. 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.
Thu 2/193:00 pmMDW - DEN
1 stop7h 17mFrontier
Mon 2/236:00 amDEN - MDW
1 stop6h 08mFrontier
Deal found 1/7$144
This CheapOair deal was found by Cheapflights users on 1/6. 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.
Thu 2/56:20 amMDW - DEN
1 stop11h 08mFrontier
Tue 2/106:00 amDEN - MDW
1 stop12h 07mFrontier
Deal found 1/6$145
This Southwest deal was found by Cheapflights users on 1/4. 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.
Tue 2/102:10 pmMDW - DEN
Nonstop2h 40mSouthwest
Sat 2/148:25 pmDEN - MDW
Nonstop2h 20mSouthwest
Deal found 1/4$148
This Frontier deal was found by Cheapflights users on 1/7. 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.
Sat 3/76:00 amMDW - DEN
1 stop12h 00mFrontier
Wed 3/111:09 pmDEN - MDW
1 stop8h 10mFrontier
Deal found 1/7$150
This Expedia deal was found by Cheapflights users on 1/5. 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.
Mon 1/129:15 amMDW - SLC
1 stop10h 12mFrontier
Fri 1/166:50 amSLC - MDW
1 stop12h 04mFrontier
Deal found 1/5$256

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Wyoming 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 January 7, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Wyoming that are best for you.

Fly from

Midway

Fly to

Wyoming

Route

Depart

Return

Price

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/17

2:05 pm-3:45 pm

Nonstop2h 40m

Denver Intl

Wed 2/18

6:25 pm-9:50 pm

Nonstop2h 25m

$155

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 4/2

9:40 pm-11:20 pm

Nonstop2h 40m

Denver Intl

Tue 4/7

6:35 am-9:55 am

Nonstop2h 20m

$159

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 3/14

9:35 pm-11:15 pm

Nonstop2h 40m

Denver Intl

Wed 3/18

6:25 am-9:50 am

Nonstop2h 25m

$167

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 3/24

5:35 pm-7:15 pm

Nonstop2h 40m

Denver Intl

Sat 3/28

5:55 am-9:20 am

Nonstop2h 25m

$167

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 2/5

2:05 pm-3:45 pm

Nonstop2h 40m

Denver Intl

Tue 2/10

4:35 pm-7:55 pm

Nonstop2h 20m

$170

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/24

2:10 pm-3:50 pm

Nonstop2h 40m

Denver Intl

Sat 2/28

7:20 am-10:55 am

Nonstop2h 35m

$170

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/31

7:40 pm-9:25 pm

Nonstop2h 45m

Denver Intl

Thu 2/5

11:05 am-2:25 pm

Nonstop2h 20m

$190

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 2/21

5:55 pm-7:40 pm

Nonstop2h 45m

Denver Intl

Mon 2/23

7:35 am-11:10 am

Nonstop2h 35m

$192

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 1/27

5:35 pm-7:20 pm

Nonstop2h 45m

Denver Intl

Wed 1/28

1:25 pm-4:45 pm

Nonstop2h 20m

$192

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 3/3

7:55 pm-9:40 pm

Nonstop2h 45m

Denver Intl

Sat 3/7

8:10 am-11:35 am

Nonstop2h 25m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 53 results
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Best time to book a flight from Midway to Wyoming

Have a flexible travel schedule? Discover the best time to fly to Wyoming from Midway 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 Chicago Midway Airport to Wyoming
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 Midway to Wyoming. 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 Chicago Midway Airport to Wyoming?

    A quick flight from Chicago Midway Airport to Wyoming can take about 2h 40m. Southwest provides one of the quickest options available for as low as $155. The distance from Chicago Midway Airport to Wyoming is about 893 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from Chicago Midway Airport to Wyoming is Chicago Midway - Denver Intl. You may also consider Chicago Midway - Salt Lake City or Chicago Midway - Jackson Hole.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Wyoming 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

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Alternative routes for Midway to Wyoming

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
O'Hare Intl to George Bush Intcntl flights

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