$5288 Cheap Flights to Chicago Midway International
One-way
Departing from
Thailand
Going to
Chicago Midway International
Chicago (MDW)
United States • November, 2025
56% AI deal score
$6,000 $5,288
This is the lowest one-way flight price found by RatePunk users in the last 24 hours for a flight departing from Chicago Midway International. Fares are subject to change and may not be available for all dates. (Data last updated 11/8/2025).
Popular airlines to Chicago Midway International
American Airlines
Air Canada
Alaska Airlines, Inc.
JetBlue Airways
Delta Air Lines
Frontier Airlines
United Airlines
Southwest Airlines
197,908 searches in the past 7 days on RatePunk
Flight deals up to 90% off
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Top Cheap Flight Deals to Chicago Midway International
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.
Number of airlines
10+ airlines
Chicago Midway International is served by more than 10 airlines, offering a mix of full-service and low-cost options; Southwest Airlines is by far the dominant carrier, but you can also find flights from Delta, Porter, and Volaris!
Typical price range (round-trip)
$80 - $400
Dreaming of deep-dish pizza and blues music? Flights to Chicago Midway can range from $80 to $400, depending on when you decide to visit the Windy City. Prices often peak during the summer months and around major holidays, so consider flying during the shoulder season for better deals!
Flight frequency
500+ Flights
Flights to Chicago Midway International Airport (MDW) are consistently available throughout the week, but you might notice a slight increase in options during peak travel seasons and popular times like early mornings and late afternoons.
MDW Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
MDW airport insights
Best days to catch a deal
Mon, Tue
Based on the data, Saturday and Sunday are the days when the cheapest flight deals to Chicago Midway International Airport are most frequently found. With deal counts of 33 and 35 respectively, these weekend days appear to offer better opportunities for savings.
Avg. deal survival time
18.7 hours
Deals from Chicago Midway International typically survive for 18.7 hours. This means you should book quickly when you find a good deal!
Rare deal frequency
16 deals
We uncovered 16 rare flight deals for Chicago Midway International Airport in the last month, all boasting an exceptional AI Deal Score of 90 or higher. These rare deals typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-71%
The average price drop for flights departing from Chicago Midway International Airport is a significant 70.9%, indicating substantial potential savings. Travelers flying from this airport can often find much lower fares compared to the initial listed prices.
Next 4 weeks: deal forecast
Chicago Midway International Airport Forecast
The forecast for Chicago Midway International Airport next month shows stable flight prices overall. There are no significant price drops or increases expected based on current trends.
Top 5 biggest price drops (last 3 months)
Found on November 6
Zacatecas - MDW
$1,180 → $159
87%
Found on November 2
South Bend - MDW
$1,275 → $185
85%
Found on November 6
Durango - MDW
$1,015 → $172
83%
Found on November 3
Vancouver - MDW
$643 → $115
82%
Found on November 4
San Salvador - MDW
$2,410 → $433
82%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Des Moines International (DSM)
~3 rare deals/month
Gerald R. Ford International (GRR)
~6 rare deals/month
General Mitchell International (MKE)
~8 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially DSM and GRR 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
Distinct
Seasonal considerations
Chicago experiences distinct seasonal price variations for flights. Summer (June-August) and the holiday season (December) tend to be pricier. Booking during the shoulder seasons (spring and fall) offers a good balance of pleasant weather and affordable flights.
TL;DR: To snag the best deal on flights to Chicago, consider flying in January and booking your trip around two months in advance, ideally on a Tuesday. Wednesday are often the cheapest days to fly. Chicago has distinct seasonal pricing, with summer and holidays being the most expensive. Planning your trip during the shoulder seasons will help you save.
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!
Tip: Arrive early, especially during peak travel times, as security lines can get long.
Other airports
Okay, so you're trying to sneak into the Windy City through a side door, huh? South Bend International Airport (SBN) in Indiana is about a 2-hour drive from Chicago, but keep in mind that traffic can be a real buzzkill. On the flip side, the South Shore Line train can drop you right into downtown, so you can avoid those pesky highways all together!
Airport transfers
Navigating Chicago's airports is a breeze with options like the 'L' train whisking you downtown, taxis and ride-shares aplenty, and shuttle services for a more budget-friendly approach. Each offers a unique blend of convenience and cost, so you can pick the one that sings to your travel tune. Prepare to dive headfirst into the city's vibrant energy as soon as you hop off your flight!
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 symphony orchestra - muti & sainz villegas
Experience Rodrigo's captivating musical portrait of the royal palace and gardens near Madrid, featuring guitarist Pablo Sáinz-Villegas. His previous CSO performance was highly praised, and this promises to be another unforgettable concert.
Chicago Weather
Weather in Chicago
Wed, Nov 5
10%
17° 3°
10%
Thu, Nov 6
10%
15° 4°
10%
Fri, Nov 7
10%
16° 7°
10%
Sat, Nov 8
45%
10° 1°
45%
Sun, Nov 9
20%
3° -2°
20%
Mon, Nov 10
35%
3° -2°
35%
Tue, Nov 11
10%
6° -1°
10%
Here’s a quick look at the weather you can expect, plus this week’s forecast:
Seasons: Chicago experiences four distinct seasons. Spring (March-May) brings milder temperatures (5-15°C, 41-59°F) and blooming flora; Summer (June-August) is warm (20-30°C, 68-86°F) and sometimes humid; Autumn (September-November) has cooler temperatures (10-20°C, 50-68°F) and colorful foliage; Winter (December-February) is cold (-5-5°C, 23-41°F) with snow.
Rain: Chicago sees rain throughout the year, with snowfall mainly from November to March. While rain is generally not impactful, heavy snowstorms in winter can cause travel delays and disruptions.
This week's forecast: From Nov 5 to Nov 9, the weather in Chicago will range from 3.1°C to 16.7°C (37.58°F to 62.06°F). Expect sunny and cloudy days with rain showers, transitioning to flurries and snow towards the end of the week.
(We update the weather forecast weekly so you know what to expect during your travel week. Always check a day or two before your flight for the most current conditions.)
Frequently Asked Questions About Flights to Chicago Midway International
(Have more questions?) Feel free to reach out or check our comprehensive Chicago Midway International travel guide. We’re here to help make your flight to Chicago Midway International (and the trip itself) as smooth as possible.
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.
Book in Advance (But Not Too Early!): Aim to book your flight about 2-3 months before your travel date. It's the sweet spot where airlines start getting antsy to fill those seats!
Set Up Price Alerts: Use RatePunk to track flight prices and get notified when they drop. It's like having a personal flight deal hunter working for you 24/7.
Mix and Match Airlines: Sometimes, booking your outbound and return flights with different airlines can save you a bundle. It's a bit more work, but your bank account will thank you.
Embrace Layover Flights: Non-stop flights are a luxury. If you're willing to endure a layover or two, you could save a significant amount on your journey to Chicago.
Clear Your Cookies (Seriously!): Airlines and booking sites sometimes track your searches and hike up prices. Clear your browser cookies or use incognito mode to see the real deals.
Red-Eye Flights: Flying at night could save you money, as fewer people want to travel at those hours. Plus, it leaves you with a full day to explore upon arrival!
Take Advantage of Budget Airlines: Check out low-cost carriers that fly into Midway. Just be aware of extra fees for luggage and seat selection.
Check Social Media for Flash Sales: Follow airlines and travel deal sites on social media. They often announce flash sales or special promotions that can save you big bucks.
By keeping these tips in mind, you’ll be well-equipped to find the cheapest flights to Chicago Midway International and make the most of your travel budget. After all, the more you save on your flight, the more you can spend on a Broadway show, a nice meal, or an extra tour in Chicago Midway International! 🎉✈️
