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Cheap flights from Wyoming to Chicago from $103

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 7/25. 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

Find the cheapest flights from Wyoming to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:40 pm - 5:05 pm
DEN
-
MDW
2h 25mnonstop
Southwest Logo
8:50 pm - 10:25 pm
MDW
-
DEN
2h 35mnonstop
$205Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
6:00 am - 9:20 am
DEN
-
MDW
2h 20mnonstop
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
$206Southwest
Sat, Aug 8 - Thu, Aug 13
Southwest Logo
8:25 pm - 11:45 pm
DEN
-
MDW
2h 20mnonstop
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
$208Southwest
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
10:09 am - 4:51 pm
DEN
-
MDW
5h 42m
1 stop
Frontier Logo
4:45 pm - 10:55 pm
MDW
-
DEN
7h 10m
1 stop
$210Frontier
Tue, Aug 11 - Wed, Aug 12
Southwest Logo
7:25 pm - 10:50 pm
DEN
-
MDW
2h 25mnonstop
Southwest Logo
2:15 pm - 6:30 pm
MDW
-
DEN
5h 15m
1 stop
$211Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
11:10 am - 5:10 pm
DEN
-
MDW
5h 00m
1 stop
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
$212Southwest
Sat, Aug 8 - Thu, Aug 13
Southwest Logo
3:15 pm - 7:45 pm
DEN
-
MDW
3h 30m
1 stop
Southwest Logo
7:35 pm - 9:10 pm
MDW
-
DEN
2h 35mnonstop
$213Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
7:02 am - 6:33 pm
JAC
-
MDW
10h 31m
2 stops
Delta Logo
1:51 pm - 8:10 pm
MDW
-
JAC
7h 19m
1 stop
$699Delta
Wed, Aug 12 - Mon, Aug 17
Delta Logo
8:35 am - 6:33 pm
JAC
-
MDW
8h 58m
2 stops
Delta Logo
1:25 pm - 8:10 pm
MDW
-
JAC
7h 45m
2 stops
$904Delta
Wed, Aug 12 - Mon, Aug 17
Delta Logo
8:35 am - 4:15 pm
JAC
-
MDW
6h 40m
1 stop
Delta Logo
1:51 pm - 8:10 pm
MDW
-
JAC
7h 19m
1 stop
$1,004Delta
Wed, Aug 12 - Mon, Aug 17

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Delta flights from Wyoming to Chicago Midway Airport

Our best Delta deals on Wyoming to Chicago Midway Airport flight tickets
Delta
Aug 25
DEN6:05 amDenver Intl
5h 34m
1 stop
MDW12:39 pmChicago Midway
Aug 26
MDW1:25 pmChicago Midway
4h 58m
1 stop
DEN5:23 pmDenver Intl
$224
Delta
Aug 12
DEN10:19 amDenver Intl
7h 14m
1 stop
MDW6:33 pmChicago Midway
Aug 15
MDW1:25 pmChicago Midway
4h 58m
1 stop
DEN5:23 pmDenver Intl
$225
Delta
Aug 14
DEN12:59 amDenver Intl
7h 18m
1 stop
MDW9:17 amChicago Midway
Aug 17
MDW7:25 pmChicago Midway
5h 09m
1 stop
DEN11:34 pmDenver Intl
$226

Frontier flights from Wyoming to Chicago Midway Airport

Our best Frontier deals on Wyoming to Chicago Midway Airport flight tickets
Frontier
Aug 11
DEN10:09 amDenver Intl
5h 42m
1 stop
MDW4:51 pmChicago Midway
Aug 12
MDW4:45 pmChicago Midway
7h 10m
1 stop
DEN10:55 pmDenver Intl
$210
Frontier
Jul 25
DEN11:59 pmDenver Intl
10h 08m
1 stop
MDW11:07 amChicago Midway
Aug 4
MDW6:05 amChicago Midway
8h 55m
1 stop
DEN2:00 pmDenver Intl
$228
Frontier
Jul 21
DEN10:09 amDenver Intl
5h 42m
1 stop
MDW4:51 pmChicago Midway
Jul 22
MDW4:45 pmChicago Midway
7h 10m
1 stop
DEN10:55 pmDenver Intl
$230

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 June 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

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 9/2

1:40 pm-5:05 pm

Nonstop2h 25m

Chicago Midway

Tue 9/8

8:50 pm-10:25 pm

Nonstop2h 35m

$205
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/8

6:00 am-9:20 am

Nonstop2h 20m

Chicago Midway

Thu 8/13

7:35 pm-9:10 pm

Nonstop2h 35m

$206

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/6

8:25 pm-11:45 pm

Nonstop2h 20m

Chicago Midway

Mon 8/10

7:35 pm-9:10 pm

Nonstop2h 35m

$208

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 8/11

10:09 am-4:51 pm

1 stop5h 42m

Chicago Midway

Wed 8/12

4:45 pm-10:55 pm

1 stop7h 10m

$210

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/12

7:25 pm-10:50 pm

Nonstop2h 25m

Chicago Midway

Sat 8/15

2:15 pm-6:30 pm

1 stop5h 15m

$211

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 8/8

11:10 am-5:10 pm

1 stop5h 00m

Chicago Midway

Thu 8/13

7:35 pm-9:10 pm

Nonstop2h 35m

$212

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/6

3:15 pm-7:45 pm

1 stop3h 30m

Chicago Midway

Mon 8/10

7:35 pm-9:10 pm

Nonstop2h 35m

$213

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 8/12

7:02 am-6:33 pm

2 stops10h 31m

Chicago Midway

Mon 8/17

1:51 pm-8:10 pm

1 stop7h 19m

$699

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 8/12

8:35 am-6:33 pm

2 stops8h 58m

Chicago Midway

Mon 8/17

1:25 pm-8:10 pm

2 stops7h 45m

$904

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 8/12

8:35 am-4:15 pm

1 stop6h 40m

Chicago Midway

Mon 8/17

1:51 pm-8:10 pm

1 stop7h 19m

$1,004

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 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 15m

Direct flights

Every day
The fastest flight from Wyoming to Chicago Midway Airport takes 2h 15m
Direct flights go from Wyoming to Chicago Midway Airport every day.
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Frequently asked questions about flying from Wyoming to Chicago Midway Airport

  • 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
Portage
Benton Harbor
Saint Joseph
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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