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$169 Flights from Jacksonville (OAJ) to Chicago Midway (MDW)

Compare Jacksonville to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Jacksonville Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best round-trip flight from Jacksonville Airport to Chicago Midway Airport? If you want to travel next month, round-trip fares start from $487. Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Jacksonville to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Jacksonville to Chicago Midway flights are currently cheapest in April.
Jan
from $359
Feb
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Mar
from $545
Apr
from $169
May
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Jun
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Jul
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Aug
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Sep
from $188
Oct
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Nov
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Dec
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Jacksonville to Chicago Midway: Alternative routes

Compare routes from Jacksonville to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

9 miles from central Chicago
ClosestCheapest
from $169
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Chicago O'Hare International

16 miles from central Chicago
Cheapest
from $169
Search flights

Chicago Dupage County

32 miles from central Chicago
Search flights

Chicago Rockford

78 miles from central Chicago
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Jacksonville to Chicago: Flight information

The things to know before you go.
Cheapest flight found$169
Cheapest month to flyApril

Finding cheap flights from Jacksonville to Chicago Midway: Frequently asked questions

The best price we found for a round-trip flight from Jacksonville to Chicago Midway is $379. 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 Jacksonville to Chicago Midway. But we found flights with one or more stops from $379.
There are no flights flying from Jacksonville to Chicago Midway, as of January 2026.
The cheapest month to fly from Jacksonville to Chicago Midway is usually June.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jacksonville Airport to Chicago Midway Airport on Monday, June 1, 2026.
No airlines currently offer direct flights between Jacksonville Airport and Chicago Midway Airport. 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 Midway 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.
Currently, Delta offers the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago Midway from Jacksonville

Looking for cheap tickets from Jacksonville to Chicago Midway? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Jacksonville to Chicago Midway. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago Midway from Jacksonville from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Jacksonville–Chicago Midway ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago Midway from Jacksonville.
  • Set up a Price Alert. You can easily track the fare of your cheap Jacksonville–Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Jacksonville and Chicago Midway? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Jacksonville and Chicago Midway. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago Midway, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Jacksonville to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Chicago Midway from Jacksonville with hotels and car rental

    Once you've secured your cheap flight ticket from Jacksonville to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago Midway or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


Plan the rest of your trip from Jacksonville to Chicago

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