Cheap Flights from Jackson-Evers International (JAN) to Chicago (CHIA)

Compare Jackson-Evers International to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Jackson-Evers International Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Jackson-Evers International Airport to Chicago? If you want to travel next month, return fares start from £253. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Jackson-Evers International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Jackson-Evers International to Chicago flights are currently cheapest in April.

Alternative Jackson-Evers International to Chicago routes

Looking for the cheapest, fastest or easiest route from Jackson-Evers International to Chicago? You could fly into the following airports instead.

Jackson to Chicago: Flight information

The things to know before you go.
Cheapest flight found£253
Cheapest month to flyMay

Finding cheap flights from Jackson-Evers International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Jackson-Evers International to Chicago is £253. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Jackson-Evers International to Chicago. But we found flights with one or more stops from £253.
As of March 2026, there are no flights flying from Jackson-Evers International to Chicago.
The cheapest month to fly from Jackson-Evers International to Chicago is usually May.
If you're flying from Jackson-Evers International Airport, the cheapest airport near Chicago is Chicago Midway – which is 9.0 miles away from the centre of Chicago. We've found flights into this airport from £253.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jackson-Evers International Airport to Chicago on Saturday, 2 May 2026.
No airlines currently offer direct flights between Jackson-Evers International Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

Flying from Jackson-Evers International Airport (JAN) to Chicago: what you need to know

  • Chicago and Jackson (where Jackson-Evers International Airport is located) are both in the UTC-5 timezone. That means there's no time difference to adjust for.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to catch your JAN to Chicago flight.

  • Planning to travel during a peak time like school or public holidays? Expect longer queues at check-in and security. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • Central Jackson to JAN is around 6 miles. Depending on traffic conditions, it'll take about 20 minutes to reach there if you're driving, ride-sharing or catching a cab.

  • Want a hassle-free start to your holiday? Stay near JAN. Whether you're taking an early flight from Jackson-Evers International Airport to Chicago or just don't want to be rushed, these hotels are worth a look:

  • Jackson-Evers International Airport gets high marks for its on-time performance. 81.39% of flights that depart JAN arrive at their destination as scheduled.

  • JAN is located at 100 International Drive, Suite 300.

How to find the cheapest flights from Jackson-Evers International Airport (JAN) to Chicago

  • £126 is the lowest price we've seen for a one-way Jackson-Evers International Airport to Chicago flight. A round-trip ticket right now is £253. Depending on the availability when you book, these fares may change.

  • Don't leave things to the last moment. You're more likely to pick up cheap flights from JAN to Chicago if you book ahead. Airlines often have some amazing early bird rates.

  • The 'Whole month' tool will show you the cheapest tickets from Jackson-Evers International Airport to Chicago across every month. It's a good way to snap up a bargain if your travel dates are flexible.

  • Snapping up a cheap flight from JAN to Chicago couldn't be easier with Price Alerts. All you need to do is set up one of these automatic notifications and we'll let you know when a new discount appears.

  • Select your ideal departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Jackson-Evers International Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes about 35 minutes to reach by car. The centre is roughly 25 miles away.

  • Getting there by public transport takes about 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Jackson-Evers International Airport to Chicago. Check in to one of these accommodation options near ORD instead:

  • Get your adventure underway by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.

  • To get the best deal, reserve your ride from O'Hare International Airport about four weeks in advance of your flight from JAN to Chicago.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Jackson-Evers International Airport to Chicago has arrived, you can make your way to the city centre in around 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • If you choose to travel on public transport, you'll reach the centre in 45 minutes or so.

  • Hang up the 'Do not disturb' sign and rest at a hotel near MDW. Here are a few options where you can kick back after your JAN to Chicago flight:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These providers are located in or around the terminal and will have you ready to go in a flash.

  • Get exactly what you want. Booking your ride from MDW four weeks in advance often means more savings and a bigger choice of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Set your sights on the city centre after your flight from Jackson-Evers International Airport to Chicago has touched down. Central Chicago is about 85 miles from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.

  • Public transport can get you there in around 4 hours 15 minutes.

  • If you don't want to travel into the centre, head for a hotel near RFD. Check in to one of these options after your JAN to Chicago flight:

  • Stay in control of the next part of your journey with a Chicago Rockford International Airport rental car. Budget, Alamo and National will get you on the road.

  • Rental agencies sometimes offer promotions for early bookings, so book your vehicle from RFD a few weeks ahead of your flight from Jackson-Evers International Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Plan your trip to Chicago in peak season if you like a lively atmosphere, but remember that hotel prices are typically higher. Alternatively, book flights from Jackson-Evers International Airport to Chicago in the low season when prices are cheaper and it's less crowded.

  • When booking your Jackson-Evers International Airport to Chicago plane ticket, think about the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you like travelling in cooler conditions, search for a cheap ticket from JAN to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • You've done Chicago, now it's time to discover other corners of United States. Travel about 280 miles south-east to Columbus to tick off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • Indianapolis is another essential stop in United States and is around 160 miles south-east of Chicago. No trip is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.