$120 Cheap Flights from Chicago (MDW) to Jackson Hole (JAC)

View $120 flight on Mon, Sep 15, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $120 for one-way flights and $254 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 1 - Sat, Oct 4
MDW
Chicago
JAC
Jackson
$254 Roundtrip, found 9 hours ago
$254
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Oct 1 from Chicago to Jackson, returning Sat, Oct 4, priced at $254 found 9 hours ago
Delta
Sat, Aug 30 - Fri, Sep 5
MDW
Chicago
JAC
Jackson
$259 Roundtrip, found 16 hours ago
$259
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Jackson, returning Fri, Sep 5, priced at $259 found 16 hours ago
Delta
Fri, Oct 3 - Sat, Oct 4
MDW
Chicago
JAC
Jackson
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 3 from Chicago to Jackson, returning Sat, Oct 4, priced at $269 found 1 day ago
Delta
Sat, Sep 13 - Tue, Sep 30
MDW
Chicago
JAC
Jackson
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 13 from Chicago to Jackson, returning Tue, Sep 30, priced at $274 found 1 day ago
Delta
Fri, Oct 3 - Fri, Oct 24
MDW
Chicago
JAC
Jackson
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 3 from Chicago to Jackson, returning Fri, Oct 24, priced at $284 found 3 days ago
Delta
Sat, Oct 18 - Fri, Nov 7
MDW
Chicago
JAC
Jackson
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Oct 18 from Chicago to Jackson, returning Fri, Nov 7, priced at $289 found 3 days ago
Delta
Sat, Sep 6 - Tue, Sep 23
MDW
Chicago
JAC
Jackson
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Chicago to Jackson, returning Tue, Sep 23, priced at $295 found 1 day ago
Delta
Wed, Oct 1 - Mon, Oct 20
MDW
Chicago
JAC
Jackson
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Oct 1 from Chicago to Jackson, returning Mon, Oct 20, priced at $299 found 3 days ago
Delta
Tue, Oct 28 - Sat, Nov 8
MDW
Chicago
JAC
Jackson
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 28 from Chicago to Jackson, returning Sat, Nov 8, priced at $304 found 3 days ago
Delta
Tue, Sep 16 - Tue, Sep 30
MDW
Chicago
JAC
Jackson
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from Chicago to Jackson, returning Tue, Sep 30, priced at $310 found 1 day ago

Alternative airports near Jackson

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Jackson Hole Airport JAC. Cheapest and Closest option available. Average driving time to city center is 14 minutes. Flights from $494
JAC
Jackson Hole Airport
CheapestClosest
Average driving time to city center14 min
Flights from $494
Flights from Chicago (MDW) to Jackson Hole (JAC)
Origin airport
Midway Intl.
Destination airport
Jackson Hole
Airlines serving
Delta
Roundtrip price
$254
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 October. 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 $120 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?
Discover the latest flight deals from MDW to JAC by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to JAC?
The cheapest flights from MDW to JAC are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to JAC?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to JAC. Sort your results by "Price (lowest to highest)" to snap up a great 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.