$49 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
$623 $87
Chicago (MDW)
United States • February, 2026
94% AI deal score
$620 $116
Chicago (MDW)
United States • February, 2026
94% AI deal score
$620 $116
Chicago (MDW)
United States • February, 2026
94% AI deal score
$760 $123
Top Cheap Flight Deals from United States to Chicago Midway International
Recent round-trip flight deals to Chicago Midway International
Thu, Feb 19 - Sun, Feb 22
Cheapest
Miami (MIA) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Miami (MIA)
Frontier Airlines airlines • Direct
$208
$58
-$150
72%
Thu, Feb 19 - Mon, Feb 23
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$155
$58
-$97
63%
Thu, Feb 12 - Mon, Feb 16
Orlando (MCO) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • Direct
$155
$58
-$97
63%
Thu, Mar 5 - Wed, Mar 11
Dallas (DFW) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Dallas (DFW)
Frontier Airlines airlines • Direct
$133
$58
-$75
56%
Thu, Feb 26 - Sat, Mar 7
Dallas (DFW) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Dallas (DFW)
Frontier Airlines airlines • Direct
$190
$58
-$132
69%
Thu, Mar 5 - Sat, Mar 14
Dallas (DFW) - Chicago (MDW)
Frontier Airlines airlines • Direct
Chicago (MDW) - Dallas (DFW)
Frontier Airlines airlines • Direct
$133
$58
-$75
56%
The cheapest time to fly to Chicago Midway International
Facts About Flights from United States 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
Tue, Wed
Based on the provided data, the best days to find a deal for Chicago Midway International Airport are Thursday and Friday. These days have the lowest counts, indicating a higher probability of finding cheaper deals.
Avg. deal survival time
6.8 hours
Deals from Chicago Midway International airport survive for 6.8 hours on average. Due to the quick turnover, it's important to book quickly when you find a deal that you like.
Rare deal frequency
15 deals
In the past month, we've discovered 15 rare flight deals for Chicago Midway International Airport. These exceptional deals, identified by an AI Deal Score of 90+, typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-68%
On average, flights departing from Chicago Midway International (MDW) experience a price decrease of 68.0%. This suggests that travelers flying from MDW have a high likelihood of finding significantly cheaper fares if they monitor prices and book at the right time.
Next 4 weeks: deal forecast
Chicago Midway International Airport - February 2026 Forecast
Based on current trends, flight prices at Chicago Midway International Airport are expected to remain stable next month. There are no significant price drops or increases anticipated for February 2026.
Top 5 biggest price drops (last 3 months)
Found on January 4
Angeles - MDW
$6,400 → $517
92%
Found on January 7
South Bend - MDW
$1,275 → $120
91%
Found on January 2
Port of Spain - MDW
$2,255 → $416
82%
Found on December 31
London - MDW
$1,925 → $353
82%
Found on January 4
Vancouver - MDW
$643 → $130
80%
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)
~8 rare deals/month
Quad City International (MLI)
~9 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 from United States 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
kim scott
Find tickets to see Kim Scott perform live at Loews Chicago Hotel on December 31, 2025, at 7:00 PM.
city of chicago christmas tree | millennium park | chicago, il | things to do in chicago
Every year, Millennium Park showcases a spectacular Christmas tree that remains a festive highlight until the new year. The enormous tree is beautifully decorated with sparkling lights, creating a magical atmosphere for all visitors.
kingston mines new year's eve blues bash
Ring in the New Year at Kingston Mines with their New Year's Eve Bash, featuring three bands, two stages, and over nine hours of non-stop live music until 3:30 AM. Your cover charge includes hats, leis, and noise makers upon entry, as well as a balloon drop to celebrate the start of a new year.
lemoyne alexander (17+ event)
Get your tickets to see The Silvertone live at Reggie's Music Joint in Chicago on New Year's Eve, December 31, 2025, at 9:00 PM.
Chicago Weather
Weather in Chicago
Tue, Jan 6
10%
8° 2°
10%
Wed, Jan 7
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.
