$113 Cheap Flights from Jacksonville International to Chicago Midway International
One-way
Departing from
Jacksonville International
Going to
Chicago Midway International
Chicago (MDW)
United States • June, 2026
44% AI deal score
$255 $113
This is the lowest one-way flight price found by RatePunk users in the last 24 hours for a flight going to Chicago Midway International. Fares are subject to change and may not be available for all dates. (Data last updated 4/1/2026).
Top Cheap Flight Deals from Jacksonville International to Chicago Midway International
Recent round-trip flight deals to Chicago Midway International
Mon, Apr 20 - Thu, Apr 23
Cheapest
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 2 stops • Philadelphia (PHL), Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 2 stops • Atlanta (ATL), Washington, D.C. (IAD)
$418
$231
-$187
45%
Mon, Apr 20 - Sat, Apr 25
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 2 stops • Philadelphia (PHL), Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 2 stops • Atlanta (ATL), Philadelphia (PHL)
$418
$238
-$180
43%
Tue, May 12 - Tue, May 19
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$418
$262
-$156
37%
Tue, May 19 - Wed, May 27
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$418
$262
-$156
37%
Tue, May 5 - Tue, May 12
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$418
$262
-$156
37%
Tue, May 12 - Wed, May 27
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$418
$262
-$156
37%
The cheapest time to fly to Chicago Midway International
Ready to jet to Chicago Midway International on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Last-Minute Flights from Jacksonville International to Chicago Midway International
Need to get to Chicago Midway International ASAP? Even if you're booking a flight on short notice, there are often last-minute deals available:
Next 2 weeks deals
Last Minute Flight Deals
We found last minute flight deals to Chicago departing in the next two weeks starting from $279.
⌛ Last-Minute
Jacksonville - MDW
A great last-minute steal for a cross-country flight.
Found 1 week ago
$4590
round-trip
Facts About Flights from Jacksonville International to Chicago
To help you plan your journey, here are some quick Chicago flight facts and tips.
Chicago airports
Chicago boasts a trio of airports catering to diverse travel needs. O'Hare International Airport (ORD), a global aviation hub, stands as one of the world's busiest airports, offering an extensive network of domestic and international flights. Closer to the city center, Chicago Midway International Airport (MDW) provides a convenient option for travelers, particularly those seeking budget-friendly fares, with a focus on domestic routes and select international destinations. Further afield, Chicago Rockford International Airport (RFD) serves as a growing cargo and passenger airport, offering an alternative for travelers in the region and a focus on cargo operations. Each airport contributes to Chicago's connectivity, providing varied options for passengers traveling to and from the Midwest.
O Hare International (ORD)
Chicago, United States
Chicago Midway International (MDW)
Chicago, United States
Chicago Rockford International (RFD)
Chicago, United States
Pro tip: search “Chicago (Any)” to see fares to all Chicago airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Chicago Midway International
Cheapest airport
Indianapolis (IND)
Indianapolis International Airport (IND) is your gateway to savings for flights to Chicago! It's known for its user-friendliness, boasting efficient security lines and a range of amenities to make your pre-flight experience a breeze. Plus, who can resist saving a few bucks for that deep-dish pizza in Chicago?
Nonstop vs. 1-stop
70+ cities
Chicago Midway International Airport (MDW) isn't just another airfield; it's a bustling secondary airport serving over 70 destinations, with popular routes connecting to major cities like Atlanta, Denver, and Las Vegas, offering a convenient alternative for travelers.
MDW Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
MDW airport insights
Best days to catch a deal
Thur, Tue
Based on the data, Sunday and Saturday are the days when the cheapest deals are most frequently found for Chicago Midway International Airport. You're most likely to find a deal on Sunday, with Saturday coming in a close second.
Avg. deal survival time
10.8 hours
Deals from Chicago Midway International Airport typically last around 10.8 hours. You'll need to act fast to snag these deals!
Rare deal frequency
17 deals
We discovered 17 rare flight deals for Chicago Midway International Airport in the last month. These rare deals had an AI Deal Score of 90+, and they usually consist of mistake fares, special promotions, or ultra-discounts.
Average price drop
-71%
The average price drop for flights arriving at Chicago Midway International Airport is 71.0%, which means travelers can potentially save a significant amount on airfare. This substantial price reduction makes Chicago Midway an attractive option for budget-conscious travelers looking for affordable flights.
Next 4 weeks: deal forecast
Chicago Midway International Airport - Next Month's Forecast
Based on current trends, flights from Chicago Midway International Airport are expected to see a slight price increase next month. Demand is anticipated to rise, so booking flights sooner rather than later is recommended.
Top 5 biggest price drops (last 3 months)
Found on March 27
Bridgetown - MDW
$3,060 → $425
86%
Found on March 25
Guatemala City - MDW
$1,070 → $168
84%
Found on March 25
Marseille - MDW
$1,725 → $351
80%
Found on March 25
Grand Junction - MDW
$783 → $157
80%
Found on March 25
Santiago de los Caballeros - MDW
$1,088 → $219
80%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Central Illinois Regional (BMI)
~9 rare deals/month
Gerald R. Ford International (GRR)
~10 rare deals/month
General Mitchell International (MKE)
~7 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially BMI and GRR for long-haul deal surprises.
When Is the Best Time to Fly from Jacksonville International to Chicago Midway International
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Chicago Midway International:
Cheapest month
January
Cheapest month
January is typically the cheapest month to fly to Chicago. Bundle up, because the Windy City lives up to its name in January! Expect fewer crowds at museums and attractions, making it a great time for a budget-friendly cultural escape.
Best day to book
Tuesday
Best day to book
Tuesday appears to be the golden day for booking flights to Chicago. Airlines often release deals early in the week, so keep your eyes peeled on Tuesdays! Booking mid-week can potentially save you some serious cash for deep dish pizza.
Cheapest days to fly
Wednesday
Cheapest days to fly
Fly to Chicago on a Wednesday to potentially save some dough. Mid-week flights are often less expensive than weekend flights. Plus, you'll beat the weekend crowds and have the city all to yourself.
Advance booking sweet spot
2 months
Advance booking sweet spot
Two months before your trip is often the sweet spot for booking flights to Chicago. Booking in advance allows you to snag better deals before prices surge. This way, you will have more money left over for all those Chicago must-dos!
Seasonal considerations
Chicago Midway International Airports & Ground Transportation
One big question for travelers is which Chicago Midway International airport to fly into. Here’s a quick guide to Chicago Midway International’s airports and how to get to the city from each:
O'Hare International Airport (ORD)
O'Hare International Airport is one of the busiest airports in the world, serving as a major hub for United and American Airlines. Located on the northwest side of Chicago, it offers a vast array of amenities including shopping, dining, and even a yoga room for travelers seeking relaxation. The airport has four terminals and numerous concourses, making it a city unto itself. Getting downtown is a breeze with the 'L' Blue Line train, which offers direct service, or you can grab a taxi or rideshare for a more direct route. Consider the train to avoid traffic!
Tip: Navigating O'Hare can be overwhelming, so download the airport map to your phone before you go.
Chicago Midway International Airport (MDW)
Located on the southwest side of Chicago, Midway International Airport is a convenient option for travelers looking to avoid the hustle and bustle of O'Hare. While smaller, it still offers a variety of amenities including restaurants, shops, and free wifi. Southwest Airlines has a large presence there. Getting to downtown Chicago is easy via the 'L' Orange Line train, which provides a direct, affordable route, or taxis and rideshares are readily available. Midway is closer to downtown than O'Hare!
What to Do in Chicago
Chicago isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Chicago, organized by interest:
Sightseeing & landmarks
Chicago's skyline is iconic! Don't miss the Cloud Gate ('The Bean') in Millennium Park, and take an architectural boat tour on the Chicago River for a unique perspective of the city's stunning buildings.
Arts & culture
Explore the Art Institute of Chicago, home to masterpieces like 'American Gothic,' or catch a Broadway-quality show in the Theater District. Chicago's vibrant music scene ranges from blues to indie rock, with legendary venues like the House of Blues.
Food & nightlife
From deep-dish pizza to Michelin-starred restaurants, Chicago is a foodie paradise! After dinner, explore the city's diverse nightlife, with trendy cocktail bars in River North or blues clubs in Lincoln Park.
Shopping & fashion
The Magnificent Mile offers high-end department stores and luxury boutiques, while Wicker Park and Bucktown are known for their independent boutiques and vintage shops. Find unique fashion pieces and support local designers!
Nearby getaways
Escape the city bustle with a trip to the Indiana Dunes National Park, just a short drive from Chicago, offering hiking trails and beautiful beaches along Lake Michigan. Alternatively, explore the charming town of Galena, known for its historic architecture and wineries.
No matter your interest – be it art, food, nightlife, or nature – Chicago has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Chicago This Month
syleena johnson
Get last-minute concert tickets to see Syleena Johnson perform at City Winery in Chicago, IL.
house calls w/ bassel darwish
House Calls presents Venezuelan selector Tony Guerra with support from Bassel Darwish!
lizzy sunshine — the den theatre
Lizzy Sunshine is forced to perform her double act alone, resulting in a chaotic and hilarious comedy show exploring addiction.
malvada saturdays
Find tickets for Malvada Saturdays at Moe's Cantina in River North, Chicago, on February 28, 2026.
Chicago Weather
Weather in Chicago
Thu, Mar 26
65%
22° -1°
65%
Fri, Mar 27
Frequently Asked Questions About Flights to Chicago Midway International
Pro Tips for Finding Cheap Flights to Chicago Midway International
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Chicago Midway International flights:
Be Flexible With Your Dates: Flying mid-week or during the off-season can dramatically lower your ticket price. Who knew Tuesdays could be so trendy for your wallet?
Consider Nearby Airports: Don't limit yourself to just Midway! Check out other airports in the Chicago area; you might find a steal by being a bit more flexible with your arrival point.
