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Cheap flights from Wyoming to Chicago from $104

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 12/5. 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.
Frontier Logo
11:48 pm - 10:58 amDEN  Denver Intl-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:03 pm - 10:33 pmMDW  Chicago Midway-DEN Denver Intl
11h 30m1 stop Atlanta Hartsfield-Jackson
$164Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
11:48 pm - 10:58 amDEN  Denver Intl-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:40 am - 2:00 pmMDW  Chicago Midway-DEN Denver Intl
8h 20m1 stop Atlanta Hartsfield-Jackson
$164Frontier
Sat, Oct 10 - Tue, Oct 13
Frontier Logo
10:44 am - 5:46 pmDEN  Denver Intl-MDW Chicago Midway
6h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:40 am - 2:00 pmMDW  Chicago Midway-DEN Denver Intl
8h 20m1 stop Atlanta Hartsfield-Jackson
$164Frontier
Tue, Oct 6 - Tue, Oct 13
Southwest Logo
5:35 pm - 8:55 pmDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:15 am - 7:55 amMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$165Southwest
Sat, Oct 10 - Sat, Oct 17
Southwest Logo
7:50 pm - 11:10 pmDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:25 pm - 8:05 pmMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$165Southwest
Tue, Oct 20 - Mon, Oct 26
Southwest Logo
7:50 pm - 11:10 pmDEN  Denver Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
9:20 pm - 11:00 pmMDW  Chicago Midway-DEN Denver Intl
2h 40mnonstop
$165Southwest
Tue, Oct 27 - Thu, Oct 29
Frontier Logo
10:44 am - 5:51 pmDEN  Denver Intl-MDW Chicago Midway
6h 07m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 9:03 pmMDW  Chicago Midway-DEN Denver Intl
15h 38m1 stop Atlanta Hartsfield-Jackson
$168Frontier
Fri, Sep 11 - Tue, Sep 15
Delta Logo
10:19 am - 4:59 pmDEN  Denver Intl-MDW Chicago Midway
5h 40m1 stop Detroit Metropolitan Wayne County
Delta Logo
7:13 pm - 11:35 pmMDW  Chicago Midway-DEN Denver Intl
5h 22m1 stop Minneapolis St Paul
$197Delta
Wed, Sep 2 - Tue, Sep 8
Delta Logo
10:19 am - 4:59 pmDEN  Denver Intl-MDW Chicago Midway
5h 40m1 stop Detroit Metropolitan Wayne County
Delta Logo
7:13 pm - 11:35 pmMDW  Chicago Midway-DEN Denver Intl
5h 22m1 stop Minneapolis St Paul
$197Delta
Sat, Sep 5 - Tue, Sep 8
Delta Logo
12:59 am - 9:17 amDEN  Denver Intl-MDW Chicago Midway
7h 18m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 1:57 pmMDW  Chicago Midway-DEN Denver Intl
5h 28m1 stop Detroit Metropolitan Wayne County
$197Delta
Fri, Sep 4 - Wed, Sep 9

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Southwest flights from Wyoming to Chicago Midway Airport

Our best Southwest deals on Wyoming to Chicago Midway Airport flight tickets
Southwest
Sep 26
DEN6:00 amDenver Intl
2h 20m
MDW9:20 amChicago Midway
Oct 3
MDW7:25 pmChicago Midway
2h 40m
DEN9:05 pmDenver Intl
$165
Southwest
Sep 21
DEN8:25 pmDenver Intl
2h 25m
MDW11:50 pmChicago Midway
Sep 22
MDW6:40 amChicago Midway
2h 30m
DEN8:10 amDenver Intl
$172
Southwest
Sep 10
DEN11:05 amDenver Intl
5h 05m
1 stop
MDW5:10 pmChicago Midway
Sep 14
MDW7:00 amChicago Midway
2h 30m
DEN8:30 amDenver Intl
$175

Frontier flights from Wyoming to Chicago Midway Airport

Our best Frontier deals on Wyoming to Chicago Midway Airport flight tickets
Frontier
Oct 10
DEN11:48 pmDenver Intl
10h 10m
1 stop
MDW10:58 amChicago Midway
Oct 13
MDW6:40 amChicago Midway
8h 20m
1 stop
DEN2:00 pmDenver Intl
$164
Frontier
Sep 11
DEN10:44 amDenver Intl
6h 07m
1 stop
MDW5:51 pmChicago Midway
Sep 15
MDW6:25 amChicago Midway
15h 38m
1 stop
DEN9:03 pmDenver Intl
$168
Frontier
Oct 20
DEN10:30 amDenver Intl
10h 28m
1 stop
MDW9:58 pmChicago Midway
Oct 24
MDW1:02 pmChicago Midway
8h 02m
1 stop
DEN8:04 pmDenver Intl
$170

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 August 13, 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 Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Fri 10/16

11:48 pm-10:58 am

1 stop10h 10m

Chicago Midway

Mon 10/19

12:03 pm-10:33 pm

1 stop11h 30m

$164

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 10/10

11:48 pm-10:58 am

1 stop10h 10m

Chicago Midway

Tue 10/13

6:40 am-2:00 pm

1 stop8h 20m

$164

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 10/6

10:44 am-5:46 pm

1 stop6h 02m

Chicago Midway

Tue 10/13

6:40 am-2:00 pm

1 stop8h 20m

$164
Quickest round-trip

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 10/10

5:35 pm-8:55 pm

Nonstop2h 20m

Chicago Midway

Sat 10/17

6:15 am-7:55 am

Nonstop2h 40m

$165

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 10/20

7:50 pm-11:10 pm

Nonstop2h 20m

Chicago Midway

Mon 10/26

6:25 pm-8:05 pm

Nonstop2h 40m

$165

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Tue 10/27

7:50 pm-11:10 pm

Nonstop2h 20m

Chicago Midway

Thu 10/29

9:20 pm-11:00 pm

Nonstop2h 40m

$165

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Fri 9/11

10:44 am-5:51 pm

1 stop6h 07m

Chicago Midway

Tue 9/15

6:25 am-9:03 pm

1 stop15h 38m

$168

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Wed 9/2

10:19 am-4:59 pm

1 stop5h 40m

Chicago Midway

Tue 9/8

7:13 pm-11:35 pm

1 stop5h 22m

$197

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Sat 9/5

10:19 am-4:59 pm

1 stop5h 40m

Chicago Midway

Tue 9/8

7:13 pm-11:35 pm

1 stop5h 22m

$197

DenverChicago

DEN Denver Intl - MDW Chicago Midway

DENMDW

Denver Intl

Fri 9/4

12:59 am-9:17 am

1 stop7h 18m

Chicago Midway

Wed 9/9

9:29 am-1:57 pm

1 stop5h 28m

$197

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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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