$92 Find Cheap Flights from Chicago to Wyoming - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Wyoming

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Jackson
Jacksonnonstop$378
Casper
Casper1 stop$318
Cody
Cody1 stop$368
Jackson
Jacksonnonstop$378
Casper
Casper1 stop$318
Cody
Cody1 stop$368
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?

Flight prices are below average for this route right now.

Flights to Wyoming from Chicago usually cost between $454 and $664 in January.
The lowest price found in the past 5 days was $378 on American Airlines (Jan 5-Jan 12).

What is the cheapest Chicago to Wyoming flight route?

The cheapest ticket to Wyoming from Chicago found in the last 5 days was to Jackson, at $355 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 $355.

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

The cheapest time of day to fly to Wyoming is generally in the afternoon, when round-trip flights cost $450 on average. Morning departures are around 3% 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 $486.

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $452 on average.

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

The cheapest month for flights from Chicago to Wyoming is April, when tickets cost $362 (return) on average. On the other hand, the most expensive months are September and December, when the average cost of round-trip tickets is $532 and $505 respectively.

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

For Chicago to Wyoming, Monday 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 get a below average price on the flight from Chicago to Wyoming, you should book around 3 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low season

November

Cheapest flight

$92
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway 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

 
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 10157 reviews
6.7Food
8.1Crew
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

2.0 MediocreWilliam, Aug 2026
Read more United Airlines reviews

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

One thing you can always count on is your AA flight getting delayed. This is not surprising when they operate these planes like a greyhound bus with wings.

The seats cushion on my seat (exit row) needs to be replaced. It felt like I was sitting on a bar rather than a seat cushion. Also, I was in the middle seat and I sat next to an oversized guy (window seat) and he took up about 25% of my space. Otherwise, the experience was good. :)

The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.

Good flight, regional jet so old and seats could use an upgrade

Couldn't make the flight because connecting flight was canceled.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

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

Cabin class types available on flights to Wyoming