$31 Cheap Flights from Chicago Midway International
One-way
Departing from
Chicago Midway International
Going to
anywhere
Asheville (AVL)
United States • November, 2025
94% AI deal score
$450 $52
New York (EWR)
United States • January, 2026
89% AI deal score
$440 $35
Toronto (YTZ)
Canada • May, 2026
89% AI deal score
$305 $56
Destin (VPS)
United States • December, 2025
86% AI deal score
$418 $53
Top Destinations Where Can You Fly from Chicago Midway International
Cheap flights from Chicago Midway International
New York, United States
TOP
Jan • Direct
$440
$35
-$405
92%
New York, United States
TOP
Jan • Direct
$440
$21
-$419
95%
New York, United States
TOP
Jan • Direct
$440
$21
-$419
95%
New York, United States
TOP
Jan • Direct
$440
$41
-$399
91%
New York, United States
TOP
Dec • Direct
$440
$21
-$419
95%
New York, United States
TOP
Dec • Direct
$440
$26
-$414
94%
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 DestinationsFacts 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, Thursday
Based on the data, Tuesday and Wednesday tend to have the best flight deals from Chicago Midway International airport. You're more likely to find a cheaper flight departing on those days compared to others when flying from Midway.
Avg. deal survival time
15.7 hours
Deals from Chicago Midway International airport last around 15.7 hours on average. This means you should book quickly if you find a flight deal you like from {{ origin_airport }}.
Rare deal frequency
20 deals
In the past month, we discovered 20 rare flight deals originating from Chicago Midway International airport. These rare deals, identified by an AI Deal Score of 90+, typically include mistake fares, special promotions, or ultra-discounts.
Average price drop
-78%
Deals that originate from Chicago Midway International airport see an average price drop of 78.0%. This means you can find significant savings on flights from Chicago Midway International.
Next 4 weeks: deal forecast
Chicago Midway Flight Forecast
Looking ahead to December 2025, flight deals from Chicago Midway International Airport are expected to remain relatively stable with a slight potential increase due to holiday travel. While some minor price drops may occur on less popular travel dates, overall prices are not anticipated to decrease significantly.
Top 5 biggest price drops (last 3 months)
Found on November 12
MDW - Paris
$6,800 → $211
97%
Found on November 9
MDW - Zacatecas
$2,380 → $239
90%
Found on November 10
MDW - Evansville
$615 → $93
85%
Found on November 12
MDW - Amsterdam
$1,345 → $232
83%
Found on November 10
MDW - Lima
$1,065 → $192
82%
Check these nearby airports too
Looking for more options? These airports near MDW sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~13 rare deals/month
General Mitchell International (MKE)
~5 rare deals/month
Chicago Rockford International (RFD)
~14 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.
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:
