Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport from $40

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find, compare and book domestic and international flights departing from Chicago Midway Airport

1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find flights from Chicago Midway Airport within your budget

 
Find flights departing from Chicago Midway Airport that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on November 6, 2025. In the last 7 days, momondo users made a total of 832,500 searches

Fly to

Route

Depart

Return

Price

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Tue 11/18

1:56 pm-4:54 pm

Nonstop1h 58m

$40

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 12/12

3:52 pm-7:40 pm

Nonstop2h 48m

$44

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Thu 12/25

6:12 am-9:30 am

Nonstop2h 18m

$44

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$48

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/9

7:44 am-9:51 pm

1 stop13h 07m

$57

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Tue 12/9

7:44 am-7:44 am

1 stop23h 00m

$57

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 12/8

5:55 pm-9:00 pm

Nonstop2h 05m

$58

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 12/9

1:40 pm-5:35 pm

Nonstop2h 55m

$66

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 12/10

5:29 pm-1:07 am

1 stop6h 38m

$80

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 11/27

9:41 am-5:36 pm

1 stop7h 55m

$89

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Where can I directly fly to from Chicago Midway Airport?

Currently, 58 destinations can be reached directly via flights from Chicago Midway Airport.

Flights from Chicago Midway Airport to

Aguascalientes

from$177

Flights from Chicago Midway Airport to

Albany, New York

from$201

Flights from Chicago Midway Airport to

Albuquerque

from$167

Flights from Chicago Midway Airport to

Asheville

from$51

Flights from Chicago Midway Airport to

Atlanta

from$54

Flights from Chicago Midway Airport to

Austin

from$98

Flights from Chicago Midway Airport to

Baltimore

from$51

Flights from Chicago Midway Airport to

Birmingham, Alabama

from$254

Flights from Chicago Midway Airport to

Boston

from$58

Flights from Chicago Midway Airport to

Buffalo

from$110

Flights from Chicago Midway Airport to

Cancún

from$114

Flights from Chicago Midway Airport to

Charleston

from$399

Flights from Chicago Midway Airport to

Charlotte

from$68

Flights from Chicago Midway Airport to

Cleveland

from$75

Flights from Chicago Midway Airport to

Denver

from$74

Flights from Chicago Midway Airport to

Durango

from$157

Flights from Chicago Midway Airport to

El Paso

from$205

Flights from Chicago Midway Airport to

Fort Lauderdale

from$125

Find the cheapest flights from Chicago Midway Airport

Cheap one-way flights from Chicago Midway Airport

Enter your travel dates to find the best prices.
Frontier Logo
1:56 pm - 4:54 pmMDW-ATL
1h 58mnonstop
$40Frontier
Find Deal
Tue, Nov 18
Frontier Logo
3:52 pm - 7:40 pmMDW-MCO
2h 48mnonstop
$44Frontier
Find Deal
Fri, Dec 12
Frontier Logo
6:12 am - 9:30 amMDW-ATL
2h 18mnonstop
$44Frontier
Find Deal
Thu, Dec 25
Frontier Logo
4:46 pm - 8:34 pmMDW-MCO
2h 48mnonstop
$48Frontier
Find Deal
Fri, Nov 28
Multiple Airlines Logo
7:44 am - 9:51 pmMDW-MCO
13h 07m1 stop
$57Multiple Airlines
Find Deal
Tue, Dec 9
Multiple Airlines Logo
7:44 am - 7:44 amMDW-ATL
23h 00m1 stop
$57Multiple Airlines
Find Deal
Tue, Dec 9
Southwest Logo
5:55 pm - 9:00 pmMDW-LGA
2h 05mnonstop
$58Southwest
Find Deal
Mon, Dec 8
Southwest Logo
1:40 pm - 5:35 pmMDW-FLL
2h 55mnonstop
$66Southwest
Find Deal
Tue, Dec 9
Delta Logo
5:29 pm - 1:07 amMDW-JFK
6h 38m1 stop
$80Delta
Find Deal
Wed, Dec 10
Delta Logo
9:41 am - 5:36 pmMDW-DFW
7h 55m1 stop
$89Delta
Find Deal
Thu, Nov 27

Flights from Chicago Midway Airport - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago Midway Airport to help you craft the best travel plan.

What are the most popular domestic flights out of Chicago Midway?

From Chicago Midway, you can take domestic flights to many cities. Searches reveal that momondo users prefer flights to Jacksonville, Charlotte, Los Angeles, Louisville, and Charleston the most.

Which international cities can I fly to direct from Chicago Midway?

There are many cities you can fly direct to from Chicago Midway. According to searches, the most popular international destinations for direct flights among momondo users are Toronto, Zacatecas, Morelia, Guadalajara and Durango.

What are the cheapest cities to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago currently is Miami at $29. The next cheapest destinations are New York, Houston, Louisville, Tampa and Pittsburgh.

Frequently asked questions regarding flights from Chicago Midway Airport

Which airlines are currently offering the cheapest flights from Chicago Midway Airport?

Our data suggests that currently, the cheapest flights from Chicago Midway Airport are being offered by Delta, Frontier, and Allegiant Air. For example, Delta flights from Chicago Midway Airport to Savannah, start at $51, Frontier flights from Chicago Midway Airport to Washington, D.C. cost around $54, and Allegiant Air flights from Chicago Midway Airport to Punta Gorda are around $74.

What is the cheapest flight available from Chicago Midway Airport?

Currently, the cheapest flight from Chicago Midway Airport found by our users is for $29 to Miami. Prices will vary according to several factors such as the departure date and time, but on average you can expect to pay around $223 to travel from Chicago Midway Airport to Miami.

Which destinations have the most frequent flights from Chicago Midway Airport?

Atlanta, Orlando Airport and Orlando are currently the destinations served most frequently from Chicago Midway Airport, with 13, 10 and 10 flights per day on average, respectively.

Which airlines can you fly with from Chicago Midway Airport?

Airlines including Southwest, Delta and Frontier frequently fly from Chicago Midway Airport. You can view other airlines by performing a quick search in the form above.

When did momondo last update prices for flights from Chicago Midway Airport?

Prices for flights from Chicago Midway Airport refresh daily.

How many operators does momondo search for flights from Chicago Midway Airport?

The number of operators available for flights from Chicago Midway Airport is 12 as of November 2025.

How old do you have to be to fly from Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Alternate flight departure points

Chicago
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 12/6
Sat 12/13
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip

Popular domestic flights from Chicago Midway Airport

Chicago to Dallas Flightsfrom $91
Chicago to Atlanta Hartsfield-Jackson Flightsfrom $58
Chicago to Orlando Flightsfrom $58
Chicago to Las Vegas Harry Reid Intl Flightsfrom $131
Chicago to Miami Flightsfrom $58
Chicago to Los Angeles Flightsfrom $130
Chicago to Phoenix Flightsfrom $58
Chicago to Washington, D.C. Flightsfrom $98
Chicago to Tampa Flightsfrom $110
Chicago to Fort Lauderdale Flightsfrom $110
Chicago to Houston Flightsfrom $81
Chicago to Seattle/Tacoma Intl Flightsfrom $157
Chicago to Denver Intl Flightsfrom $127
Chicago to New Orleans Louis Armstrong Flightsfrom $154
Chicago to San Francisco Flightsfrom $130
Chicago to Fort Myers SW Florida Intl Flightsfrom $124
Chicago to Philadelphia Flightsfrom $137
Chicago to Minneapolis St Paul Flightsfrom $97
Chicago to Boston Logan Intl Flightsfrom $117
Chicago to New York Flightsfrom $59