$28 Cheap Flights from Chicago Midway International
One-way
Departing from
Chicago Midway International
Going to
anywhere
Knoxville (TYS)
United States • May, 2026
93% AI deal score
$483 $56
Destin (VPS)
United States • April, 2026
90% AI deal score
$385 $50
Toronto (YTZ)
Canada • April, 2026
87% AI deal score
$305 $71
New York (EWR)
United States • April, 2026
84% AI deal score
$258 $28
Top Destinations Where Can You Fly from Chicago Midway International
Cheap flights from Chicago Midway International
Find flights from Chicago Midway International to anywhere
Looking for inspiration on destinations? Here are some popular flight deals from Chicago Midway International one-way fares:
See more destinations you can fly to from Chicago Midway International – anywhere in the world at the best prices.
See More DestinationsLast-Minute Flights from Chicago Midway International
The best flight deals leaving from Chicago Midway International soon
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - San Juan (SJU)
Frontier Airlines airlines • 2 stops • Atlanta (ATL), Orlando (MCO)
$395
$177
-$218
55%
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - Madrid (MAD)
KLM airlines • 3 stops • Atlanta (ATL), New York (JFK), Manchester (MAN)
$915
$337
-$578
63%
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - Houston (IAH)
Frontier Airlines airlines • Direct
$215
$79
-$136
63%
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - Denver (DEN)
Frontier Airlines airlines • 1 stop • Dallas (DFW)
$115
$170
+$55
48%
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - San Juan (SJU)
Frontier Airlines airlines • 2 stops • Dallas (DFW), Tampa (TPA)
$395
$167
-$228
58%
Mon, Mar 2
⌛ Last-Minute
Chicago (MDW) - Rio de Janeiro (GIG)
LATAM Chile airlines • 1 stop • Atlanta (ATL)
$860
$289
-$571
66%
Facts About Flights from Chicago Midway International
Nearby airport(s)
Insights for flights from Chicago Midway International
Most popular airlines from Chicago Midway International
American Airlines
Alaska Airlines, Inc.
JetBlue Airways
Delta Air Lines
MDW Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
MDW airport insights
Best days to catch a deal
Friday, Tuesday
Based on the data, the best days to find flight deals from Chicago Midway International airport are Wednesdays and Saturdays. You have a higher chance of securing a cheaper flight deal when departing from Midway on these days.
Avg. deal survival time
11.4 hours
Deals from Chicago Midway International airport typically last around 11.4 hours. So, if you see a great fare from {{airport name}}, you should book it quickly.
Rare deal frequency
5 deals
We found 5 rare deals originating from Chicago Midway International Airport in the past month. These rare deals had an AI Deal Score of 90+, and are usually mistake fares, special promotions or ultra-discounts.
Average price drop
-77%
Deals that originate from Chicago Midway International airport see an average price drop of 76.9%. This means travelers can find significant savings on flights from Chicago Midway International.
Next 4 weeks: deal forecast
Chicago Midway Flight Forecast
Based on our analysis, flights from Chicago Midway International (MDW) are expected to remain relatively stable in price next month. There may be slight fluctuations, but no major price drops or increases are currently anticipated.
Top 5 biggest price drops (last 3 months)
Found on February 13
MDW - Paris
$16,400 → $270
98%
Found on February 13
MDW - Morelia
$2,735 → $195
93%
Found on February 16
MDW - London
$1,650 → $236
86%
Found on February 13
MDW - Buenos Aires
$1,250 → $267
79%
Found on February 16
MDW - Bogotá
$768 → $159
79%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Central Illinois Regional (BMI)
~5 rare deals/month
General Mitchell International (MKE)
~5 rare deals/month
Chicago Rockford International (RFD)
~10 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially BMI and MKE for long-haul deal surprises.
Travel Trends: Popular Destinations from Chicago Midway International
Every month, we analyze search and booking data to see where travelers from Chicago Midway International are heading. Here are the current hot destinations from Chicago Midway International:
Top domestic destinations
Orlando
TOP
Chicago Midway International
Las Vegas
TOP
Chicago Midway International
Miami
TOP
Chicago Midway International
These cities are seeing the most searches and bookings from Chicago Midway International this month.
Top international destinations
Travelers from Chicago Midway International are flocking here, possibly due to seasonal events or great deals.
Travel trend insight
Chicago travelers are increasingly drawn to destinations rich in history and culture. London and Rome remain top international choices due to their iconic landmarks, historical significance, and diverse cultural experiences, offering a blend of traditional attractions and modern amenities that appeal to a wide range of travelers.
Booking Flights from Chicago Midway International: Frequently Asked Questions
Pro Tips for Finding Cheap Flights from Chicago Midway International
Finding the cheapest airfare from Chicago Midway International is easier if you use a few smart strategies. Here are our top tips to help you score a great deal:
Be Flexible with Your Dates: If your travel dates aren't set in stone, you can save big! Flying on Tuesdays, Wednesdays, or Saturdays is often cheaper than flying on weekends or Mondays due to lower demand.
Feeling adventurous? Type "Anywhere" into your destination and let the cheap flight deals guide your next getaway! You might discover a dream destination you never considered.
Explore More Destinations from Chicago Midway International
Looking for more options? Here are some popular routes and related travel deals:
