$106 Find Cheap Flights from Chicago to Wyoming - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Wyoming departing on 8/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Chicago to Wyoming

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Jackson
Jackson1 stop$369
Casper
Casper1 stop$308
Cody
Cody1 stop$298
Jackson
Jackson1 stop$369
Casper
Casper1 stop$308
Cody
Cody1 stop$298

Book Cheap Chicago to Wyoming Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Wyoming that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Wyoming

Tue, Sep 29 - Wed, Sep 30
Southwest Logo
9:00 am - 12:55 pm
MDW
-
DEN
4h 55m
1 stop
Southwest Logo
11:15 am - 4:00 pm
DEN
-
MDW
3h 45m
1 stop
$170Southwest
Wed, Aug 19 - Mon, Aug 24
Frontier Logo
7:05 am - 9:44 pm
ORD
-
DEN
15h 39m
2 stops
Frontier Logo
9:55 am - 1:36 pm
DEN
-
ORD
2h 41mnonstop
$170Frontier
Tue, Aug 18 - Mon, Aug 24
Southwest Logo
9:00 am - 12:55 pm
MDW
-
DEN
4h 55m
1 stop
Southwest Logo
4:55 pm - 8:15 pm
DEN
-
MDW
2h 20mnonstop
$171Southwest
Sat, Nov 7 - Sun, Nov 15
Frontier Logo
11:06 am - 1:00 pm
ORD
-
DEN
2h 54mnonstop
Frontier Logo
5:56 pm - 9:35 pm
DEN
-
ORD
2h 39mnonstop
$171Frontier
Sat, Aug 8 - Thu, Aug 13
United Airlines Logo
5:00 am - 9:28 am
ORD
-
COD
5h 28m
1 stop
United Airlines Logo
5:53 pm - 11:59 pm
COD
-
ORD
5h 06m
1 stop
$298United Airlines
Sat, Aug 22 - Sat, Aug 29
United Airlines Logo
1:30 pm - 5:17 pm
ORD
-
LAR
4h 47m
1 stop
United Airlines Logo
5:30 am - 11:28 am
LAR
-
ORD
4h 58m
1 stop
$304United Airlines
Tue, Aug 18 - Sun, Aug 30
Delta Logo
7:48 am - 12:27 pm
ORD
-
WYS
5h 39m
1 stop
Delta Logo
1:09 pm - 9:33 pm
WYS
-
ORD
7h 24m
1 stop
$304Delta
Sun, Aug 23 - Sun, Aug 30
Delta Logo
6:00 am - 12:27 pm
ORD
-
WYS
7h 27m
2 stops
Delta Logo
1:09 pm - 9:33 pm
WYS
-
ORD
7h 24m
1 stop
$314Delta
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
10:00 am - 12:15 pm
ORD
-
JAC
3h 15mnonstop
American Airlines Logo
3:38 pm - 8:05 pm
JAC
-
ORD
3h 27mnonstop
$373American Airlines
Mon, Aug 10 - Mon, Aug 17
American Airlines Logo
5:00 am - 10:12 am
ORD
-
JAC
6h 12m
1 stop
American Airlines Logo
4:30 pm - 12:18 am
JAC
-
ORD
6h 48m
1 stop
$375American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Wyoming flights

Get data-powered insights and trends into flights from Chicago to Wyoming to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Wyoming?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Wyoming departing in August.

What is the cheapest Chicago to Wyoming flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Wyoming from Chicago found in the last 5 days was to Jackson, at $374 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Jackson (JAC), and the cheapest round-trip airline ticket found on this route in the last 5 days was $374.

What is the cheapest time of day to fly to Wyoming?

The average price for all round-trip flights from Chicago to Wyoming depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Wyoming is generally in the afternoon, when round-trip flights cost $439 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Wyoming is generally in the morning, which is peak travel time and where the average cost of a ticket is $481.

Can I save money by flying with a layover from Chicago to Wyoming?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $501, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Wyoming?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Wyoming, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Wyoming is September, when tickets cost $191 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $346 and $319 respectively.

What’s the cheapest day of the week to fly from Chicago to Wyoming?

The average price of all round-trip flights from Chicago to Wyoming clicked on KAYAK for each day over the last 12 months.

For Chicago to Wyoming, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Wyoming back to Chicago, the best deals are generally found on Wednesday, with Sunday being the most expensive.

How far in advance should I book a flight from Chicago to Wyoming?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Wyoming, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Wyoming, you should book around 5 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$106
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to Denver

FAQs - booking Wyoming flights

  • How does KAYAK find such low prices on flights from Chicago to Wyoming?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Wyoming.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Wyoming?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Wyoming is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Wyoming?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Wyoming with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Wyoming?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Wyoming up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Wyoming

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Wyoming. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Wyoming? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9948 reviews
6.7Food
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

6.0 GoodMatthew, Jul 2026
ORD - SEA
Read more United Airlines reviews

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

Everything you need to know for your flight from Chicago to Wyoming

Cabin class types available on flights to Wyoming

Cabin classes available on flights to Wyoming. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.