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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 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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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 January 14, 2026. In the last 7 days, momondo users made a total of 832,500 searches

Fly to

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$44

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$45

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sat 3/28

9:16 pm-11:59 pm

Nonstop2h 43m

$49

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sun 2/8

5:13 pm-8:00 pm

Nonstop2h 47m

$54

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/6

8:00 am-12:15 pm

Nonstop3h 15m

$55

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sun 2/8

5:13 pm-8:00 pm

Nonstop2h 47m

$56

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 4/10

8:00 am-12:15 pm

Nonstop3h 15m

$56

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 2/16

9:22 pm-1:09 am

Nonstop2h 47m

$56

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 2/25

7:00 am-8:07 pm

1 stop12h 07m

$64

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 2/17

6:15 pm-10:05 pm

Nonstop2h 50m

$79

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Where can I directly fly to from Chicago Midway Airport?

Currently, 56 destinations can be reached directly via flights from Chicago Midway Airport.

Flights from Chicago Midway Airport to

Aguascalientes

from$140

Flights from Chicago Midway Airport to

Albany, New York

from$111

Flights from Chicago Midway Airport to

Albuquerque

from$311

Flights from Chicago Midway Airport to

Asheville

from$140

Flights from Chicago Midway Airport to

Austin

from$88

Flights from Chicago Midway Airport to

Baltimore

from$104

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$96

Flights from Chicago Midway Airport to

Durango

from$171

Flights from Chicago Midway Airport to

El Paso

from$171

Flights from Chicago Midway Airport to

Fort Lauderdale

from$118

Flights from Chicago Midway Airport to

Fort Myers

from$89

Flights from Chicago Midway Airport to

Guadalajara

from$104

Flights from Chicago Midway Airport to

Hartford

from$78

Flights from Chicago Midway Airport to

Jacksonville

from$239

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
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$44Frontier
Sun, Jan 18
Frontier Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$45Frontier
Sun, Jan 18
Frontier Logo
9:16 pm - 11:59 pm
MDW
-
DFW
2h 43mnonstop
$49Frontier
Sat, Mar 28
Frontier Logo
5:13 pm - 8:00 pm
MDW
-
DFW
2h 47mnonstop
$54Frontier
Sun, Feb 8
Frontier Logo
8:00 am - 12:15 pm
MDW
-
MIA
3h 15mnonstop
$55Frontier
Mon, Apr 6
Frontier Logo
5:13 pm - 8:00 pm
MDW
-
DFW
2h 47mnonstop
$56Frontier
Sun, Feb 8
Frontier Logo
8:00 am - 12:15 pm
MDW
-
MIA
3h 15mnonstop
$56Frontier
Fri, Apr 10
Frontier Logo
9:22 pm - 1:09 am
MDW
-
MCO
2h 47mnonstop
$56Frontier
Mon, Feb 16
Multiple Airlines Logo
7:00 am - 8:07 pm
MDW
-
MCO
12h 07m
1 stop
$64Multiple Airlines
Wed, Feb 25
Southwest Logo
6:15 pm - 10:05 pm
MDW
-
RSW
2h 50mnonstop
$79Southwest
Tue, Feb 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?

From Chicago Midway, you can take domestic flights to many cities. Searches reveal that momondo users prefer flights to Tampa, Detroit, Los Angeles, San Diego, and Jacksonville 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, Guadalajara, Cancún, Morelia 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 Dallas, Phoenix, Charlotte, Houston and Raleigh.

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 $202 to travel from Chicago Midway Airport to Miami.

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

Atlanta, Detroit Metropolitan Wayne County Airport and Detroit are currently the destinations served most frequently from Chicago Midway Airport, with 21, 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 January 2026.

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 $145
Chicago to Orlando Flightsfrom $73
Chicago to Fort Lauderdale Flightsfrom $128
Chicago to Las Vegas Harry Reid Intl Flightsfrom $143
Chicago to Dallas Flightsfrom $72
Chicago to Miami Flightsfrom $105
Chicago to Phoenix Flightsfrom $59
Chicago to New York Flightsfrom $106
Chicago to Tampa Flightsfrom $157
Chicago to Atlanta Hartsfield-Jackson Flightsfrom $64
Chicago to Denver Intl Flightsfrom $159
Chicago to Fort Myers SW Florida Intl Flightsfrom $140
Chicago to San Francisco Flightsfrom $161
Chicago to Houston Flightsfrom $115
Chicago to New Orleans Louis Armstrong Flightsfrom $157
Chicago to Santa Ana J. Wayne/Orange Cnty Flightsfrom $173
Chicago to Honolulu Flightsfrom $362
Chicago to San Diego Flightsfrom $148
Chicago to Seattle/Tacoma Intl Flightsfrom $163
Chicago to Palm Beach Intl Flightsfrom $139