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$127 Cheap Flights from Jackson (MKL) to Chicago (ORD)

View $127 flight on Tue, Sep 22, 2026Opens in a new window

Popular airlines from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Jackson to Chicago (MKL-ORD)

Prices were available within the past 7 days and start at $127 for one-way flights and $254 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Sep 22 - Fri, Sep 25
MKL
Jackson
ORD
Chicago
$254 Roundtrip, found 1 hour ago
$254
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Sep 22 from Jackson to Chicago, returning Fri, Sep 25, priced at $254 found 1 hour ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Sep 24 - Sun, Sep 27
MKL
Jackson
ORD
Chicago
$264 Roundtrip, found 5 hours ago
$264
Roundtrip
found 5 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Sep 24 from Jackson to Chicago, returning Sun, Sep 27, priced at $264 found 5 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Aug 20 - Mon, Aug 24
MKL
Jackson
ORD
Chicago
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $274 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Aug 20 - Wed, Aug 26
MKL
Jackson
ORD
Chicago
$285 Roundtrip, just found
$285
Roundtrip
just found
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 20 from Jackson to Chicago, returning Wed, Aug 26, priced at $285 just found
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Aug 20 - Sun, Aug 23
MKL
Jackson
ORD
Chicago
$295 Roundtrip, found 7 hours ago
$295
Roundtrip
found 7 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 20 from Jackson to Chicago, returning Sun, Aug 23, priced at $295 found 7 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Aug 2 - Sun, Aug 16
MKL
Jackson
ORD
Chicago
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Aug 2 from Jackson to Chicago, returning Sun, Aug 16, priced at $315 found 2 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Aug 14 - Sun, Aug 16
MKL
Jackson
ORD
Chicago
$316 Roundtrip, found 2 hours ago
$316
Roundtrip
found 2 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 14 from Jackson to Chicago, returning Sun, Aug 16, priced at $316 found 2 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Aug 9 - Thu, Aug 13
MKL
Jackson
ORD
Chicago
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Aug 9 from Jackson to Chicago, returning Thu, Aug 13, priced at $336 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Sep 3 - Tue, Sep 8
MKL
Jackson
ORD
Chicago
$355 Roundtrip, found 2 hours ago
$355
Roundtrip
found 2 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Sep 3 from Jackson to Chicago, returning Tue, Sep 8, priced at $355 found 2 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Aug 8 - Sun, Aug 9
MKL
Jackson
ORD
Chicago
$356 Roundtrip, found 6 hours ago
$356
Roundtrip
found 6 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Aug 8 from Jackson to Chicago, returning Sun, Aug 9, priced at $356 found 6 hours ago

What you need to know for your flight from McKellar-Sipes Regional to O'Hare Intl.

Jackson (MKL) to Chicago (ORD) at a glance

Travel from Jackson (MKL) to Chicago (ORD) on this convenient domestic short-haul route with a full-service airline. Explore Chicago's iconic attractions and vibrant neighborhoods as you find the best itinerary for your travel plans. Check out the essential details for flights from McKellar-Sipes Regional Airport to O'Hare International Airport, making your journey from Jackson to Chicago seamless and enjoyable.

  • Fastest flight duration: around 1h 45m non-stop
  • Route distance: roughly 450 miles (725 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $80–$205, depending on seasonality and how far ahead you book

Flights from McKellar-Sipes Regional Airport (MKL) to O'Hare International Airport (ORD)

Based on recent traveler bookings, here are the top airlines favored for non-stop flights from Jackson to Chicago. These options allow you to easily compare prices, total travel times, and cabin classes, helping you to create the ideal travel itinerary to meet your needs.

  • Key Lime DBA Denver Air Connection: This comprehensive carrier provides direct flights, with one-way ticket prices generally falling between $80 and $205. It handles nearly all departures on this route, with a total travel duration of 1 hour and 45 minutes.

Best time to fly from Jackson (MKL) to Chicago (ORD)

The most popular months for travelers flying from Jackson to Chicago are February, March, and December, when peak temperatures in Chicago reach up to 37°F in March. If you prefer quieter travel, consider October, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 54.9°F. For better deals, December usually offers the lowest average one-way fare around $96. Flight availability peaks in November, with approximately 8 flights per week, making it easier to find convenient departure times.

  • Cheapest time to fly: December usually offers good deals with average one-way fare around $96, roughly 25% cheaper than the yearly average.
  • Most flight options: November has the highest number of flights from Jackson to Chicago, with approximately 8 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)Average7$121
February27.0°F (-2.8°C)High7$112
March37.0°F (2.8°C)High7$132
April46.0°F (7.8°C)Average7$141
May57.0°F (13.9°C)Average7$134
June67.3°F (19.6°C)Average7$124
July73.4°F (23.0°C)Low7$148
August73.0°F (22.8°C)Low7$135
September67.1°F (19.5°C)Average7$138
October54.9°F (12.7°C)Low7$134
November42.3°F (5.7°C)Average8$133
December33.1°F (0.6°C)High7$96

*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 (MKL) to Chicago (ORD)

  • Jackson to Chicago (MKL-MDW): Midway International Airport (MDW) lies approximately 16 miles from O'Hare International Airport (ORD), making it a convenient choice for travelers.

How to find the best prices for flights from Jackson (MKL) to Chicago (ORD)

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. Departures in the afternoon (12 PM to 6 PM) often offer lower prices, while morning flights (5 AM to 12 PM) are the most popular. Additionally, flying on Monday typically provides cheaper prices, whereas Friday is 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 O'Hare International Airport from McKellar-Sipes Regional Airport

Chicago welcomes travelers from Jackson with a range of transport options based on price, convenience, and proximity. 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 O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare 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 O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is approximately 2.2 miles from the airport and is best accessed by car.

Frequently asked questions

How much does a flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $127 and cheap return flights from $254 Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $79 and $591, and return flights often range between $171 and $778. 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
December is the cheapest month to fly from Jackson, TN (MKL) to Chicago, IL (ORD), with average return fares around $173. This is about 21% lower than the average price throughout the year, as demand is lower during the holiday season. Other budget-friendly months include January and March.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Key Lime Air operates around 7 direct flights from MKL to ORD every week.
What is the cheapest airline that flies from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Key Lime Air is one of the cheapest airlines offering connecting flights from Jackson, TN (MKL) to Chicago, IL (ORD) with return tickets starting from around $513. 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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 airline to fly with from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Jackson, TN (MKL) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, Key Lime Air offers early morning flights. If price is the most important factor, Key Lime Air typically offers the lowest fares. Key Lime Air offers the most daily flights from Jackson to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Jackson, TN (MKL) to Chicago, IL (ORD), December and January are the best months to fly. Return flights during these months average around $173, making them quite affordable. December is festive with holiday activities, while January offers a quieter travel experience. This recommendation is based on booking data from the past year.*Prices based on flights available on Expedia in the last year.
How many flights per day from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 1 nonstop flights per day from McKellar-Sipes Regional (MKL) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from MKL to ORD. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Jackson, TN (MKL) to Chicago, IL (ORD) are in the early morning, from 6am to 9am. About 68% of passengers prefer this time window. Many major carriers, including SkyWest and American Airlines, offer flights during this window. This timing is popular because it allows you to arrive in Chicago early and make the most of your day.
How long does it take to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from MKL to ORD takes around 1 hour 50 minutes, with the route covering approximately 444 miles. Flights with a layover typically take 7 hours 10 minutes longer than direct options. 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for MKL to ORD 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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 McKellar-Sipes Regional (MKL)?
From McKellar-Sipes Regional (MKL), you can fly into O'Hare Intl. (ORD) to reach Chicago. Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL) 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare 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
McKellar-Sipes Regional
Destination airport
O'Hare Intl.
Airlines serving
KEY LIME AIR DBA DENVER AIR CONNECTION
Roundtrip price
$248
Distance
443 mi
Average flight time
1 hour 40 mins

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 September. 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 $127 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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