$221 Cheap Flights from Chicago (MDW) to Jackson Hole (JAC)

View $221 flight on Sat, Sep 5, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Jackson Hole Airport (JAC)

Cheap Flights from Chicago to Jackson Hole (MDW-JAC)

Prices were available within the past 7 days and start at $221 for one-way flights and $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jan 9 - Sat, Jan 24
MDW
Chicago
JAC
Jackson
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 9 from Chicago to Jackson, returning Sat, Jan 24, priced at $309 found 3 days ago
Delta
Wed, Jan 7 - Sat, Jan 24
MDW
Chicago
JAC
Jackson
$314 Roundtrip, found 3 days ago
$314
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jan 7 from Chicago to Jackson, returning Sat, Jan 24, priced at $314 found 3 days ago
Delta
Tue, Dec 2 - Sun, Dec 7
MDW
Chicago
JAC
Jackson
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Jackson, returning Sun, Dec 7, priced at $319 found 2 days ago
Delta
Wed, Dec 24 - Fri, Jan 9
MDW
Chicago
JAC
Jackson
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 24 from Chicago to Jackson, returning Fri, Jan 9, priced at $325 found 3 days ago
Delta
Tue, Dec 2 - Wed, Dec 17
MDW
Chicago
JAC
Jackson
$330 Roundtrip, found 3 days ago
$330
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Jackson, returning Wed, Dec 17, priced at $330 found 3 days ago
Delta
Fri, Jan 9 - Mon, Jan 26
MDW
Chicago
JAC
Jackson
$334 Roundtrip, found 3 days ago
$334
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 9 from Chicago to Jackson, returning Mon, Jan 26, priced at $334 found 3 days ago
Delta
Tue, Jan 13 - Fri, Jan 16
MDW
Chicago
JAC
Jackson
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 13 from Chicago to Jackson, returning Fri, Jan 16, priced at $336 found 1 day ago
Delta
Fri, Jan 9 - Fri, Jan 23
MDW
Chicago
JAC
Jackson
$339 Roundtrip, found 3 days ago
$339
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 9 from Chicago to Jackson, returning Fri, Jan 23, priced at $339 found 3 days ago
Delta
Wed, Jan 7 - Mon, Jan 26
MDW
Chicago
JAC
Jackson
$339 Roundtrip, found 3 days ago
$339
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jan 7 from Chicago to Jackson, returning Mon, Jan 26, priced at $339 found 3 days ago
Delta
Tue, Jan 13 - Thu, Jan 22
MDW
Chicago
JAC
Jackson
$341 Roundtrip, found 1 day ago
$341
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 13 from Chicago to Jackson, returning Thu, Jan 22, priced at $341 found 1 day ago
Flights from Chicago (MDW) to Jackson Hole (JAC)
Origin airport
Midway Intl.
Destination airport
Jackson Hole
Airlines serving
Delta
Roundtrip price
$308
Distance
1170 mi

Chicago to Jackson Hole Flights

The cheapest times to fly from Chicago to Jackson Hole

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Jackson Hole are during the month of January. You can find some of the cheapest flights from Chicago to Jackson Hole with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Jackson Hole

Sunday is one of the best days to book for cheap flights from Chicago to Jackson Hole: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Jackson Hole

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Jackson Hole in 2025. You can also book with separate airlines for your outbound and return journeys, from $221 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Jackson Hole flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Jackson Hole airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC) cost?
Grab a cheap one-way flight from $221 or cheap return flight from $309 from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
January is the most affordable month to fly from MDW to JAC. Traveling outside of peak seasons is often the key to better flight prices.
Which airlines fly direct from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
You can't take a direct flight from Chicago, IL (MDW-Midway Intl.) to Jackson Hole Airport (JAC). However, you can easily reach Jackson without any layovers by leaving from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from MDW to JAC. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
Direct flights from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to JAC?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
Opt for a flight from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC) that leaves before 3 PM to reduce the likelihood of delays. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC) last-minute?
Last-minute fares from MDW to JAC are usually more expensive. To lock in the best prices, start searching for flights well in advance. That said, if you're flexible with your travel dates, you may score a cheap ticket right before you leave.
Is it cheaper to book a MDW to JAC flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to JAC flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one convenient place will take the stress out of travel planning. Just secure your flights and select from our extensive range of hotels, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Jackson Hole Airport (JAC)?
It's generally possible to reschedule or cancel your MDW to JAC flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.