$59 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 $59
Miami (MIA)
United States • February, 2026
92% AI deal score
$990 $174
New York (EWR)
United States • January, 2026
92% AI deal score
$2,640 $174
Orlando (MCO)
United States • February, 2026
90% AI deal score
$1,230 $174
Top Destinations Where Can You Fly from Chicago Midway International
Cheap flights from Chicago Midway International
Knoxville, United States
TOP
May • Direct
$483
$59
-$424
88%
New York, United States
TOP
Jan • Direct
$440
$29
-$411
93%
New York, United States
TOP
Jan • Direct
$440
$31
-$409
93%
Destin, United States
TOP
Mar • Direct
$385
$57
-$328
85%
Orlando, United States
TOP
Feb • Direct
$205
$29
-$176
86%
Orlando, United States
TOP
Jan • Direct
$205
$29
-$176
86%
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, Jan 12
⌛ Last-Minute
Chicago (MDW) - Orlando (MCO)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$205
$115
-$90
44%
Mon, Jan 12
⌛ Last-Minute
Chicago (MDW) - Denver (DEN)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$213
$81
-$132
62%
Mon, Jan 12
⌛ Last-Minute
Chicago (MDW) - Denver (DEN)
Frontier Airlines airlines • 2 stops • Atlanta (ATL), Raleigh (RDU)
$213
$169
-$44
21%
Mon, Jan 12
⌛ Last-Minute
Chicago (MDW) - Santo Domingo (SDQ)
Frontier Airlines airlines • 3 stops • Atlanta (ATL), Raleigh (RDU), New York (EWR)
$270
$339
+$69
26%
Mon, Jan 12
⌛ Last-Minute
Chicago (MDW) - Denver (DEN)
Frontier Airlines airlines • 1 stop • Atlanta (ATL)
$213
$131
-$82
38%
Mon, Jan 12
⌛ Last-Minute
Chicago (MDW) - Santiago de Chile (SCL)
LATAM Chile airlines • 2 stops • Atlanta (ATL), Lima (LIM)
$1,160
$469
-$691
60%
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
Monday, Thursday
Based on the data, Monday is the best day to find deals for flights originating from Chicago Midway International airport. Sunday has the second-lowest count, suggesting it may also present an opportunity to find cheaper flights from Chicago Midway.
Avg. deal survival time
13.2 hours
The average flight deal from Chicago Midway International Airport lasts about 13.2 hours. Therefore, it's important to book quickly when you find a deal you like from Chicago Midway International Airport to ensure you don't miss out.
Rare deal frequency
5 deals
We found 5 rare flight deals originating from Chicago Midway International Airport in the past month. These deals received an AI Deal Score of 90+ and typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-73%
On average, deals that originate from Chicago Midway International airport see a price drop of 72.6%. This means travelers can save a significant amount on flights from Chicago Midway International airport by monitoring deals.
Next 4 weeks: deal forecast
Chicago Midway Flight Forecast: Next Month
Based on current trends as of 1/2/2026, flight deals from Chicago Midway International are expected to remain relatively stable next month. There are no major price drops or increases anticipated at this time.
Top 5 biggest price drops (last 3 months)
Found on December 29
MDW - Paris
$1,950 → $225
88%
Found on January 1
MDW - Milan
$1,650 → $226
86%
Found on December 29
MDW - Aguascalientes
$920 → $159
83%
Found on December 29
MDW - Amsterdam
$1,345 → $222
83%
Found on December 29
MDW - Barcelona
$1,125 → $207
82%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Central Illinois Regional (BMI)
~4 rare deals/month
Gerald R. Ford International (GRR)
~4 rare deals/month
General Mitchell International (MKE)
~6 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.
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:
