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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 4/13. 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 February 12, 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

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

$40

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/22

6:15 am-10:28 am

Nonstop3h 13m

$43

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/22

6:15 am-10:28 am

Nonstop3h 13m

$44

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 3/12

4:55 pm-7:38 pm

Nonstop2h 43m

$44

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sat 5/2

11:40 am-3:35 pm

Nonstop2h 55m

$56

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 2/24

6:10 am-11:29 pm

1 stop16h 19m

$57

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 4/18

5:30 am-8:30 am

Nonstop2h 00m

$58

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 3/4

7:15 am-5:02 pm

1 stop8h 47m

$59

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 4/18

5:21 pm-11:06 pm

1 stop5h 45m

$104

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 3/31

10:45 am-4:32 pm

1 stop5h 47m

$109

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Where can I directly fly to from Chicago Midway Airport?

Currently, 57 destinations can be reached directly via flights from Chicago Midway Airport.

Flights from Chicago Midway Airport to

Aguascalientes

from$80

Flights from Chicago Midway Airport to

Albany, New York

from$293

Flights from Chicago Midway Airport to

Asheville

from$140

Flights from Chicago Midway Airport to

Austin

from$124

Flights from Chicago Midway Airport to

Baltimore

from$114

Flights from Chicago Midway Airport to

Boston

from$59

Flights from Chicago Midway Airport to

Burbank

from$151

Flights from Chicago Midway Airport to

Cancún

from$168

Flights from Chicago Midway Airport to

Charleston

from$122

Flights from Chicago Midway Airport to

Charlotte

from$64

Flights from Chicago Midway Airport to

Cincinnati

from$255

Flights from Chicago Midway Airport to

Cleveland

from$85

Flights from Chicago Midway Airport to

Denver

from$111

Flights from Chicago Midway Airport to

Durango

from$124

Flights from Chicago Midway Airport to

Fort Lauderdale

from$143

Flights from Chicago Midway Airport to

Fort Myers

from$89

Flights from Chicago Midway Airport to

Hartford

from$107

Flights from Chicago Midway Airport to

Indianapolis

from$148

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
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
$40Frontier
Mon, Apr 13
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$43Frontier
Sun, Feb 22
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$44Frontier
Sun, Feb 22
Frontier Logo
4:55 pm - 7:38 pm
MDW
-
DFW
2h 43mnonstop
$44Frontier
Thu, Mar 12
Southwest Logo
11:40 am - 3:35 pm
MDW
-
FLL
2h 55mnonstop
$56Southwest
Sat, May 2
Multiple Airlines Logo
6:10 am - 11:29 pm
MDW
-
FLL
16h 19m
1 stop
$57Multiple Airlines
Tue, Feb 24
Southwest Logo
5:30 am - 8:30 am
MDW
-
LGA
2h 00mnonstop
$58Southwest
Sat, Apr 18
Multiple Airlines Logo
7:15 am - 5:02 pm
MDW
-
FLL
8h 47m
1 stop
$59Multiple Airlines
Wed, Mar 4
Delta Logo
5:21 pm - 11:06 pm
MDW
-
HOU
5h 45m
1 stop
$104Delta
Sat, Apr 18
Delta Logo
10:45 am - 4:32 pm
MDW
-
HOU
5h 47m
1 stop
$109Delta
Tue, Mar 31

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?

Departing from Chicago Midway, the top domestic flight destinations, based on momondo users' searches, include Dallas, Charlotte, Louisville, Jacksonville, and Charleston.

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

There are many cities a direct flight away from Chicago Midway. The most popular international destinations among momondo users are Guadalajara, León, Guanajuato, Morelia, Cancún, and Zacatecas.

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

The cheapest city to fly to from Chicago currently is Dallas at $23. The next cheapest destinations are New York, Miami, Phoenix, Orlando and Punta Gorda.

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 Porter Airlines. For example, Delta flights from Chicago Midway Airport to Orlando Airport, start at $35, Frontier flights from Chicago Midway Airport to Washington, D.C. cost around $46, and Porter Airlines flights from Chicago Midway Airport to Montreal are around $69.

What is the cheapest flight available from Chicago Midway Airport?

Currently, the cheapest flight from Chicago Midway Airport found by our users is for $23 to Dallas/Fort Worth Airport. Prices will vary according to several factors such as the departure date and time, but on average you can expect to pay around $122 to travel from Chicago Midway Airport to Dallas/Fort Worth Airport.

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

Atlanta, Detroit and Detroit Metropolitan Wayne County Airport are currently the destinations served most frequently from Chicago Midway Airport, with 19, 9 and 9 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.

What is the cheapest first class flight from Chicago Midway Airport?

If you are looking for a cheap first class flight, consider flights to Atlanta, for which the starting price of a first class seat can be as low as $604.

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 February 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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