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Cheap flights from Wyoming to Chicago from $89

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wyoming to Chicago departing on 4/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Wyoming to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:35 am - 9:55 am
DEN
-
MDW
2h 20mnonstop
Southwest Logo
8:50 pm - 10:35 pm
MDW
-
DEN
2h 45mnonstop
$175Southwest
Mon, Apr 20 - Wed, Apr 22
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
3:07 pm - 9:09 pm
MDW
-
DEN
7h 02m
1 stop
$176Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
11:59 pm - 4:13 pm
DEN
-
MDW
15h 14m
1 stop
Frontier Logo
2:00 pm - 8:11 am
MDW
-
DEN
19h 11m
1 stop
$178Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
7:54 pm - 1:00 pm
DEN
-
MDW
40h 06m
2 stops
Frontier Logo
8:25 am - 4:53 pm
MDW
-
DEN
9h 28m
1 stop
$179Frontier
Thu, Apr 23 - Thu, Apr 30
Frontier Logo
11:54 pm - 11:09 am
DEN
-
MDW
10h 15m
1 stop
Frontier Logo
3:07 pm - 11:48 pm
MDW
-
DEN
9h 41m
1 stop
$180Frontier
Thu, May 7 - Mon, May 11
Southwest Logo
11:05 am - 4:35 pm
DEN
-
MDW
4h 30m
1 stop
Southwest Logo
6:00 am - 7:40 am
MDW
-
DEN
2h 40mnonstop
$181Southwest
Tue, Apr 21 - Sat, Apr 25
Frontier Logo
11:54 pm - 11:04 am
DEN
-
MDW
10h 10m
1 stop
Frontier Logo
3:07 pm - 11:48 pm
MDW
-
DEN
9h 41m
1 stop
$182Frontier
Fri, May 8 - Mon, May 11
Delta Logo
7:20 am - 5:58 pm
JAC
-
MDW
9h 38m
2 stops
Delta Logo
9:27 am - 7:01 pm
MDW
-
JAC
10h 34m
2 stops
$379Delta
Sat, Apr 25 - Sat, May 2
Delta Logo
7:20 am - 6:40 pm
JAC
-
MDW
10h 20m
2 stops
Delta Logo
6:00 am - 4:47 pm
MDW
-
JAC
11h 47m
2 stops
$478Delta
Tue, Apr 7 - Thu, Apr 9
Delta Logo
1:09 pm - 10:28 pm
JAC
-
MDW
8h 19m
2 stops
Delta Logo
1:59 pm - 8:15 pm
MDW
-
JAC
7h 16m
1 stop
$499Delta
Wed, May 6 - Sat, May 9

Delta flights from Wyoming to Chicago Midway Airport

Our best Delta deals on Wyoming to Chicago Midway Airport flight tickets
Delta
May 30
DEN6:05 amDenver Intl
5h 37m
1 stop
MDW12:42 pmChicago Midway
May 30
MDW5:10 pmChicago Midway
8h 23m
1 stop
DEN12:33 amDenver Intl
$211
Delta
Apr 9
DEN12:35 amDenver Intl
7h 18m
1 stop
MDW8:53 amChicago Midway
Apr 14
MDW9:29 amChicago Midway
5h 56m
1 stop
DEN2:25 pmDenver Intl
$287
Delta
Apr 9
DEN6:20 amDenver Intl
6h 04m
1 stop
MDW1:24 pmChicago Midway
Apr 13
MDW1:24 pmChicago Midway
4h 57m
1 stop
DEN5:21 pmDenver Intl
$294

Frontier flights from Wyoming to Chicago Midway Airport

Our best Frontier deals on Wyoming to Chicago Midway Airport flight tickets
Frontier
May 7
DEN11:54 pmDenver Intl
10h 15m
1 stop
MDW11:09 amChicago Midway
May 11
MDW3:07 pmChicago Midway
7h 02m
1 stop
DEN9:09 pmDenver Intl
$176
Frontier
Apr 24
DEN11:59 pmDenver Intl
15h 14m
1 stop
MDW4:13 pmChicago Midway
Apr 26
MDW2:00 pmChicago Midway
19h 11m
1 stop
DEN8:11 amDenver Intl
$178
Frontier
Apr 23
DEN7:54 pmDenver Intl
40h 06m
2 stops
MDW1:00 pmChicago Midway
Apr 30
MDW8:25 amChicago Midway
9h 28m
1 stop
DEN4:53 pmDenver Intl
$179

momondo Fare Finder

 
Customize your flight search to find flights from Wyoming to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated March 29, 2026.
Use the filters below to find and compare flights from Wyoming to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 4/20

6:35 am-9:55 am

Nonstop2h 20m

Chicago Midway

Wed 4/22

8:50 pm-10:35 pm

Nonstop2h 45m

$175

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/7

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Mon 5/11

3:07 pm-9:09 pm

1 stop7h 02m

$176

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 4/24

11:59 pm-4:13 pm

1 stop15h 14m

Chicago Midway

Sun 4/26

2:00 pm-8:11 am

1 stop19h 11m

$178

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 4/23

7:54 pm-1:00 pm

2 stops40h 06m

Chicago Midway

Thu 4/30

8:25 am-4:53 pm

1 stop9h 28m

$179

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/7

11:54 pm-11:09 am

1 stop10h 15m

Chicago Midway

Mon 5/11

3:07 pm-11:48 pm

1 stop9h 41m

$180

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/21

11:05 am-4:35 pm

1 stop4h 30m

Chicago Midway

Sat 4/25

6:00 am-7:40 am

Nonstop2h 40m

$181

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 5/8

11:54 pm-11:04 am

1 stop10h 10m

Chicago Midway

Mon 5/11

3:07 pm-11:48 pm

1 stop9h 41m

$182

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sat 4/25

7:20 am-5:58 pm

2 stops9h 38m

Chicago Midway

Sat 5/2

9:27 am-7:01 pm

2 stops10h 34m

$379

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 4/7

7:20 am-6:40 pm

2 stops10h 20m

Chicago Midway

Thu 4/9

6:00 am-4:47 pm

2 stops11h 47m

$478

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 5/6

1:09 pm-10:28 pm

2 stops8h 19m

Chicago Midway

Sat 5/9

1:59 pm-8:15 pm

1 stop7h 16m

$499

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Wyoming to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Wyoming to Chicago Midway?

Southwest, Frontier, and Delta are the most popular carriers operating from Wyoming to Chicago Midway

Cheap Wyoming to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wyoming to Chicago Midway Airport

Fastest flight time

2h 20m

Direct flights

Every day
The fastest flight from Wyoming to Chicago Midway Airport takes 2h 20m
Direct flights go from Wyoming to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Wyoming to Chicago Midway Airport?

    Prices for flights from Wyoming to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Wyoming to Chicago Midway Airport?

  • How old do you have to be to fly from Wyoming to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Wyoming to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Wyoming to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Wyoming to Chicago for you.

Can I find flights from Wyoming to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Wyoming with this policy.

How can momondo help me find flights from Wyoming to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Wyoming. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wyoming to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wyoming to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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