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Cheap flights from Chicago Midway Airport from $44

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 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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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 December 22, 2025. In the last 7 days, momondo users made a total of 832,500 searches

Fly to

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 2/20

7:45 am-10:37 am

Nonstop2h 52m

$44

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 1/23

9:45 am-12:30 pm

Nonstop2h 45m

$45

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 1/30

9:45 am-12:30 pm

Nonstop2h 45m

$46

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sun 1/18

11:05 am-1:48 pm

Nonstop2h 43m

$50

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sun 1/18

11:05 am-1:48 pm

Nonstop2h 43m

$51

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sat 2/21

9:15 am-11:26 pm

1 stop13h 11m

$61

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 1/20

1:35 pm-5:30 pm

Nonstop2h 55m

$66

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 2/11

7:15 pm-10:20 pm

Nonstop2h 05m

$70

ChicagoPhoenix

MDW - PHX

MDWPHX

Chicago Midway

Sat 2/14

7:15 pm-10:15 pm

Nonstop4h 00m

$74

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 1/17

5:35 pm-8:40 pm

Nonstop2h 05m

$75

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Where can I directly fly to from Chicago Midway Airport?

Currently, 55 destinations can be reached directly via flights from Chicago Midway Airport.

Flights from Chicago Midway Airport to

Aguascalientes

from$213

Flights from Chicago Midway Airport to

Albany, New York

from$300

Flights from Chicago Midway Airport to

Albuquerque

from$204

Flights from Chicago Midway Airport to

Asheville

from$87

Flights from Chicago Midway Airport to

Atlanta

from$34

Flights from Chicago Midway Airport to

Austin

from$138

Flights from Chicago Midway Airport to

Baltimore

from$40

Flights from Chicago Midway Airport to

Boston

from$63

Flights from Chicago Midway Airport to

Cancún

from$97

Flights from Chicago Midway Airport to

Charlotte

from$45

Flights from Chicago Midway Airport to

Cleveland

from$88

Flights from Chicago Midway Airport to

Denver

from$88

Flights from Chicago Midway Airport to

Durango

from$171

Flights from Chicago Midway Airport to

El Paso

from$386

Flights from Chicago Midway Airport to

Fort Lauderdale

from$117

Flights from Chicago Midway Airport to

Fort Myers

from$157

Flights from Chicago Midway Airport to

Guadalajara

from$183

Flights from Chicago Midway Airport to

Hartford

from$78

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
7:45 am - 10:37 am
MDW
-
DFW
2h 52mnonstop
$44Frontier
Fri, Feb 20
Frontier Logo
9:45 am - 12:30 pm
MDW
-
DFW
2h 45mnonstop
$45Frontier
Fri, Jan 23
Frontier Logo
9:45 am - 12:30 pm
MDW
-
DFW
2h 45mnonstop
$46Frontier
Fri, Jan 30
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
$50Frontier
Sun, Jan 18
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
$51Frontier
Sun, Jan 18
Multiple Airlines Logo
9:15 am - 11:26 pm
MDW
-
FLL
13h 11m1 stop
$61Multiple Airlines
Sat, Feb 21
Southwest Logo
1:35 pm - 5:30 pm
MDW
-
FLL
2h 55mnonstop
$66Southwest
Tue, Jan 20
Southwest Logo
7:15 pm - 10:20 pm
MDW
-
LGA
2h 05mnonstop
$70Southwest
Wed, Feb 11
Southwest Logo
7:15 pm - 10:15 pm
MDW
-
PHX
4h 00mnonstop
$74Southwest
Sat, Feb 14
Southwest Logo
5:35 pm - 8:40 pm
MDW
-
LGA
2h 05mnonstop
$75Southwest
Sat, Jan 17

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?

According to searches, the most popular destinations for domestic flights from Chicago Midway among momondo users are Detroit, Fort Lauderdale, Jacksonville, Los Angeles and San Diego.

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

momondo search trends show that the most popular international cities to visit when flying direct from Chicago Midway include Morelia, León, Guanajuato, Guadalajara, Zacatecas, and Cancún.

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, Atlanta, Houston, Washington, D.C. and Charlotte.

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 American Airlines. For example, Delta flights from Chicago Midway Airport to Fort Lauderdale, start at $39, Frontier flights from Chicago Midway Airport to Washington, D.C. cost around $54, and American Airlines flights from Chicago Midway Airport to Miami are around $58.

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 $158 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 22, 11 and 11 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 December 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

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Find better results for your trip

Popular domestic flights from Chicago Midway Airport

Chicago to Los Angeles Flightsfrom $154
Chicago to Orlando Flightsfrom $63
Chicago to Fort Lauderdale Flightsfrom $122
Chicago to Las Vegas Harry Reid Intl Flightsfrom $145
Chicago to Dallas Flightsfrom $70
Chicago to Miami Flightsfrom $58
Chicago to Phoenix Flightsfrom $66
Chicago to New York Flightsfrom $114
Chicago to Tampa Flightsfrom $141
Chicago to Atlanta Hartsfield-Jackson Flightsfrom $98
Chicago to Denver Intl Flightsfrom $145
Chicago to Fort Myers SW Florida Intl Flightsfrom $155
Chicago to San Francisco Flightsfrom $195
Chicago to Houston Flightsfrom $89
Chicago to New Orleans Louis Armstrong Flightsfrom $157
Chicago to Santa Ana J. Wayne/Orange Cnty Flightsfrom $191
Chicago to Honolulu Flightsfrom $423
Chicago to San Diego Flightsfrom $144
Chicago to Seattle/Tacoma Intl Flightsfrom $132
Chicago to Palm Beach Intl Flightsfrom $155