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$152 Cheap Flights from Jackson (JAN) to Chicago (MDW)

View $152 flight on Thu, Oct 1, 2026Opens in a new window

Popular airlines from Evers Intl. Airport (JAN) to Chicago Midway Airport (MDW)

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Cheap Flights from Jackson to Chicago (JAN-MDW)

Prices were available within the past 7 days and start at $152 for one-way flights and $240 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 28 - Tue, Nov 3
JAN
Jackson
MDW
Chicago
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Tue, Nov 3, priced at $240 found 5 days ago
Southwest Airlines
Sat, Sep 5 - Tue, Sep 8
JAN
Jackson
MDW
Chicago
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Jackson to Chicago, returning Tue, Sep 8, priced at $250 found 3 days ago
Southwest Airlines
Sat, Sep 5 - Tue, Sep 8
JAN
Jackson
MDW
Chicago
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Jackson to Chicago, returning Tue, Sep 8, priced at $250 found 3 days ago
Southwest Airlines
Wed, Oct 28 - Tue, Nov 3
JAN
Jackson
MDW
Chicago
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Tue, Nov 3, priced at $251 found 5 days ago
Southwest Airlines
Sat, Sep 5 - Tue, Sep 8
JAN
Jackson
MDW
Chicago
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Jackson to Chicago, returning Tue, Sep 8, priced at $256 found 3 days ago
Southwest Airlines
Thu, Aug 27 - Mon, Aug 31
JAN
Jackson
MDW
Chicago
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 27 from Jackson to Chicago, returning Mon, Aug 31, priced at $257 found 6 days ago
Southwest Airlines
Thu, Sep 17 - Thu, Oct 1
JAN
Jackson
MDW
Chicago
$258 Roundtrip, found 5 days ago
$258
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Jackson to Chicago, returning Thu, Oct 1, priced at $258 found 5 days ago
Southwest Airlines
Thu, Aug 27 - Mon, Aug 31
JAN
Jackson
MDW
Chicago
$263 Roundtrip, found 6 days ago
$263
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 27 from Jackson to Chicago, returning Mon, Aug 31, priced at $263 found 6 days ago
Southwest Airlines
Thu, Aug 27 - Mon, Aug 31
JAN
Jackson
MDW
Chicago
$268 Roundtrip, found 6 days ago
$268
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 27 from Jackson to Chicago, returning Mon, Aug 31, priced at $268 found 6 days ago
Delta
Wed, Aug 12 - Thu, Aug 13
JAN
Jackson
MDW
Chicago
$299 Roundtrip, found 6 days ago
$299
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 12 from Jackson to Chicago, returning Thu, Aug 13, priced at $299 found 6 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $467
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $467

Find the cheapest month to fly from Jackson (JAN) to Chicago (MDW)

August is typically the cheapest month to fly

From $240 - $392 per traveler.

What you need to know for your flight from Evers Intl. to Midway Intl.

Jackson (JAN) to Chicago (MDW) at a glance

Travel from Jackson (JAN) to Chicago (MDW) with a selection of airlines providing diverse options for this short domestic route. Evaluate various carriers to find the best flights from Jackson to Chicago that suit your budget and schedule while you explore the iconic attractions and neighborhoods of Chicago. Discover essential details about weekly flights from Evers International Airport to Midway International Airport as you plan your journey.

  • Fastest flight duration: around 3h 15m in-flight, plus roughly 1h 15m layover with one stop
  • Route distance: roughly 700 miles (1,130 km)
  • Flights per week: around 9 departures on average
  • Typical fares (one-way): economy tickets often range from $120–$450, depending on seasonality and how far ahead you book

Flights from Evers International Airport (JAN) to Midway International Airport (MDW)

Based on recent traveler bookings, here are the top airlines flying from Jackson to Chicago, often favored for their one-stop services. Common layover points include Hartsfield-Jackson Atlanta International Airport (ATL) with a layover of about 1 hour and 15 minutes, Nashville International Airport (BNA) at approximately 1 hour and 45 minutes, and William P. Hobby Airport (HOU) with a 1-hour layover. These options allow you to mix and match price, travel time, and cabin class to secure the best itinerary.

  • Delta: As a comprehensive carrier, Delta provides one-stop service with one-way ticket prices usually between $135 and $465. This airline represents nearly 51% of the departures for this route, featuring a flight duration of 3 hours and 15 minutes, and a total travel time of about 4 hours and 45 minutes, including the layover.
  • Southwest Airlines: Known for its budget-friendly options, Southwest Airlines also offers one-stop service, with one-way fares generally ranging from $120 to $405. This carrier accounts for about 49% of the departures on this route, with an in-flight duration of 3 hours and 15 minutes and a complete journey time of approximately 4 hours and 45 minutes, factoring in the layover.

Travelers flying from Jackson to Chicago can opt for an upgrade, as Delta provides premium economy class service on this route.

Best time to fly from Jackson (JAN) to Chicago (MDW)

The most popular months for travelers flying from Jackson to Chicago are February, March, and August, when peak temperatures in Chicago reach up to 73°F in August. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 67.1°F and typically the lowest average one-way fare (around $223). Flight availability peaks in November and December, with approximately 11 flights per week, making it easier to find convenient departure times. June has the fewest flights, with approximately 7 flights per week.

  • Cheapest time to fly: September usually offers good deals with average one-way fare around $223, roughly 18% cheaper than the yearly average.
  • More budget-friendly months to fly: May and June typically offer average one-way fares of around $237.
  • Most flight options: November and December have the highest number of flights from Jackson to Chicago, with approximately 11 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January25.7°F (-3.5°C)Average9$276
February27.0°F (-2.8°C)Slightly High8$295
March37.0°F (2.8°C)Slightly High9$333
April46.0°F (7.8°C)Average9$323
May57.0°F (13.9°C)Average9$237
June67.3°F (19.6°C)Slightly Low7$237
July73.4°F (23.0°C)Slightly Low8$251
August73.0°F (22.8°C)Slightly High10$250
September67.1°F (19.5°C)Slightly Low10$223
October54.9°F (12.7°C)Average8$260
November42.3°F (5.7°C)Average11$297
December33.1°F (0.6°C)Average11$289

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Jackson (JAN) to Chicago (MDW)

  • Jackson to Chicago (JAN-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). For one-way economy tickets on this route, prices generally fall between $125 and $410, influenced by the season and how far in advance you book. Travelers can choose from both one-stop and multi-stop flights, with common layover spots being Hartsfield-Jackson Atlanta International Airport (ATL) and Dallas-Fort Worth International Airport (DFW). Major airlines operating on this route include American Airlines and Delta, with first-class service also offered.

How to find the best prices for flights from Jackson (JAN) to Chicago (MDW)

Getting some of the best deals on flights from Jackson to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking at least two months in advance, although most travelers tend to book within two weeks. Evening departures from 6 PM to 12 AM often offer cheaper prices, while afternoon flights from 12 PM to 6 PM are the most popular. Additionally, flying on Tuesday typically results in lower fares, but Thursday remains the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Evers International Airport

Chicago welcomes travelers from Jackson with a range of transport options based on price, convenience, and proximity. For departures, Evers International Airport is roughly a 15-minute drive (covering about 13 miles) from central Jackson. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, travelers will find Midway Station, a metro station, just about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is located approximately 4.1 miles from the airport by car. Additionally, Lyons Seaport, a seaport, is around 7.2 miles away by car.

Frequently asked questions

How much does a flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $152 and cheap return flights from $240 Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $154 and $527, and return flights often range between $292 and $810. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
September is the cheapest month to fly from Jackson, MS (JAN) to Chicago, IL (MDW), with average return fares around $286. This is about 30% lower than the average price throughout the year, as travel demand tends to drop after the summer. Other budget-friendly months include January and February.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter JAN to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering connecting flights from Jackson, MS (JAN) to Chicago, IL (MDW) with a layover in William P. Hobby (HOU) starting from around $500. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Jackson (JAN) to Chicago (MDW), September and January are the best months to travel, with average return flight prices around $286. These months offer lower fares and a comfortable travel experience. If you're looking for popular travel times, August and July are also great options, providing plenty of flight choices.*Prices based on flights available on Expedia in the last year.
What is the earliest flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs at around 5:10 AM, operated by Southwest Airlines. This seasonal service is available during the summer months, giving you an early start to your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
For flights from Jackson, MS (JAN) to Chicago, IL (MDW), the most popular departure times are in the early afternoon, from noon to 3pm. About 26% of passengers prefer this time window. Southwest Airlines and Delta Air Lines offer flights during this window. This timing works well because it allows you to have a relaxed morning before your flight.
How long does it take to fly from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flying from JAN to MDW with a connection usually takes about 4 hours 20 minutes, traveling roughly 667 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for JAN to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Evers Intl. (JAN)?
When traveling from Evers Intl. (JAN) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like George Bush Intercontinental (IAH), William P. Hobby (HOU), Dallas-Fort Worth Intl. (DFW) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Jackson, MS (JAN-Evers Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Evers Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$240
Distance
667 mi

Book with confidence

Jackson to Chicago Flights

The cheapest times to fly from Jackson to Chicago

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 Jackson to Chicago are during the month of October. You can find some of the cheapest flights from Jackson to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jackson to Chicago

Sunday is one of the best days to book for cheap flights from Jackson to Chicago: 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 Jackson to Chicago

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 Jackson to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $152 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 Jackson to Chicago 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 Jackson to Chicago 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.

 

Jackson to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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