$41 Cheap Flights to Chicago Midway International
One-way
Departing from
United States
Going to
Chicago Midway International
Chicago (MDW)
United States • February, 2026
94% AI deal score
$760 $81
Chicago (MDW)
United States • February, 2026
91% AI deal score
$510 $57
Chicago (MDW)
United States • December, 2025
90% AI deal score
$653 $80
Chicago (MDW)
United States • December, 2025
89% AI deal score
$455 $56
Top Cheap Flight Deals to Chicago Midway International
Recent round-trip flight deals to Chicago Midway International
Fri, Feb 13 - Fri, Feb 20
Cheapest
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
Fri, Feb 13 - Sat, Feb 21
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
Sat, Feb 14 - Mon, Feb 23
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
Fri, Feb 13 - Sun, Feb 22
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
Fri, Feb 13 - Mon, Feb 23
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
Fri, Feb 13 - Sat, Feb 28
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$170
$48
-$122
72%
The cheapest time to fly to Chicago Midway International
Facts About Flights 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
Wed, Tue
Based on the data, Wednesday has the highest count, indicating it's the day when the most cheap flight deals are found for Chicago Midway International Airport. Saturday has the lowest count, so it may be the worst day to find a deal.
Avg. deal survival time
12.0 hours
Deals from Chicago Midway International typically last around 12.0 hours. This means you should book quickly if you find a deal you like from Chicago Midway International.
Rare deal frequency
7 deals
In the past month, we've discovered 7 rare deals for Chicago Midway International Airport. These exceptional deals, identified by an AI Deal Score of 90+, typically arise from mistake fares, special promotions, or ultra-discounts.
Average price drop
-71%
The average price drop for flights from Chicago Midway International Airport is an impressive 71.4%, indicating a significant opportunity for savings. This substantial decrease suggests that travelers flying from this airport can often find deals well below the initial listed prices.
Next 4 weeks: deal forecast
Chicago Midway Flight Forecast
Looking ahead to December 2025, flights from Chicago Midway International are expected to see a slight increase due to the holiday season, but there might be a dip in prices during the first week of December before the major holiday travel rush.
Top 5 biggest price drops (last 3 months)
Found on November 17
South Bend - MDW
$1,275 → $97
92%
Found on November 19
Port of Spain - MDW
$2,255 → $241
89%
Found on November 18
Okinawa Island - MDW
$3,375 → $458
86%
Found on November 19
Edinburgh - MDW
$2,200 → $328
85%
Found on November 17
Washington, D.C. - MDW
$675 → $107
84%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~11 rare deals/month
General Mitchell International (MKE)
~3 rare deals/month
Chicago Rockford International (RFD)
~11 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially GRR and MKE for long-haul deal surprises.
When Is the Best Time to Fly 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 Airports & Ground Transportation
One big question for travelers is which Chicago airport to fly into. Here’s a quick guide to Chicago’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
social mixer: cocktails & conversations @ the moxy
Join Windy City Social for an evening of mixing, mingling, and enjoying delicious cocktails with fellow young professional singles and new friends. Whether you're new in town or a seasoned Chicagoan, this is a great opportunity to expand your social circle and make new connections.
norman brown
Gametime offers last-minute concert tickets to see Norman Brown perform live at City Winery in Chicago, Illinois. Don't miss this chance to experience his smooth jazz stylings in an intimate setting.
smif-n-wessun
Find tickets to see Smif-N-Wessun perform live at City Winery Chicago on November 6, 2025, at 7:30 PM. Get ready for a night of classic hip-hop from these legendary artists.
glenn jones
Find tickets to see Glenn Jones perform live at City Winery Chicago on November 7, 2025, at 7:30 PM. Experience an evening of soulful music with this acclaimed R&B vocalist.
Chicago Weather
Weather in Chicago
Wed, Nov 19
10%
7° 6°
10%
Thu, Nov 20
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.
