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Cheap flights from Chicago Midway Airport from $55

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 7/3. 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 June 26, 2026. In the last 7 days, momondo users made a total of 832,500 searches

Fly to

Route

Depart

Return

Price

Cheapest one-way

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Fri 7/3

6:00 am-9:19 am

Nonstop2h 19m

$55

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Tue 6/30

6:00 am-9:19 am

Nonstop2h 19m

$56
Quickest one-way

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Tue 9/22

12:03 pm-3:03 pm

Nonstop2h 00m

$61

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 8/12

5:10 am-8:10 am

Nonstop2h 00m

$94

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 9/20

5:25 am-8:25 am

Nonstop2h 00m

$99

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 8/15

9:24 am-3:59 pm

1 stop5h 35m

$104

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 8/9

5:25 am-8:25 am

Nonstop2h 00m

$104

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 9/22

1:19 pm-7:30 pm

1 stop5h 11m

$105

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 7/18

8:00 am-10:30 pm

2 stops13h 30m

$107

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/19

11:35 am-7:05 pm

1 stop6h 30m

$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, 65 destinations can be reached directly via flights from Chicago Midway Airport.

Flights from Chicago Midway Airport to

Aguascalientes

from$105

Flights from Chicago Midway Airport to

Albany, New York

from$174

Flights from Chicago Midway Airport to

Asheville

from$58

Flights from Chicago Midway Airport to

Atlanta

from$67

Flights from Chicago Midway Airport to

Austin

from$152

Flights from Chicago Midway Airport to

Baltimore

from$98

Flights from Chicago Midway Airport to

Birmingham, Alabama

from$205

Flights from Chicago Midway Airport to

Boise

from$229

Flights from Chicago Midway Airport to

Boston

from$102

Flights from Chicago Midway Airport to

Buffalo

from$145

Flights from Chicago Midway Airport to

Burbank

from$240

Flights from Chicago Midway Airport to

Cancún

from$190

Flights from Chicago Midway Airport to

Charleston

from$278

Flights from Chicago Midway Airport to

Charlotte

from$125

Flights from Chicago Midway Airport to

Cincinnati

from$88

Flights from Chicago Midway Airport to

Cleveland

from$68

Flights from Chicago Midway Airport to

Denver

from$108

Flights from Chicago Midway Airport to

Des Moines

from$417

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
6:00 am - 9:19 am
MDW
-
ATL
2h 19mnonstop
$55Frontier
Fri, Jul 3
Frontier Logo
6:00 am - 9:19 am
MDW
-
ATL
2h 19mnonstop
$56Frontier
Tue, Jun 30
Frontier Logo
12:03 pm - 3:03 pm
MDW
-
ATL
2h 00mnonstop
$61Frontier
Tue, Sep 22
Southwest Logo
5:10 am - 8:10 am
MDW
-
LGA
2h 00mnonstop
$94Southwest
Wed, Aug 12
Southwest Logo
5:25 am - 8:25 am
MDW
-
LGA
2h 00mnonstop
$99Southwest
Sun, Sep 20
Delta Logo
9:24 am - 3:59 pm
MDW
-
EWR
5h 35m
1 stop
$104Delta
Sat, Aug 15
Southwest Logo
5:25 am - 8:25 am
MDW
-
LGA
2h 00mnonstop
$104Southwest
Sun, Aug 9
Delta Logo
1:19 pm - 7:30 pm
MDW
-
EWR
5h 11m
1 stop
$105Delta
Tue, Sep 22
Southwest Logo
8:00 am - 10:30 pm
MDW
-
MIA
13h 30m
2 stops
$107Southwest
Sat, Jul 18
Delta Logo
11:35 am - 7:05 pm
MDW
-
MIA
6h 30m
1 stop
$109Delta
Sat, Sep 19

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, St. Louis, Charlotte, El Paso, 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, San Luis Potosí, Morelia, León, Guanajuato and Guadalajara.

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

The cheapest city to fly to from Chicago currently is Valparaiso at $49. The next cheapest destinations are Knoxville, Asheville, Houston, Atlanta and St. Louis.

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, Allegiant Air, and American Airlines. For example, Delta flights from Chicago Midway Airport to Newark Airport, start at $56, Allegiant Air flights from Chicago Midway Airport to Asheville cost around $58, and American Airlines flights from Chicago Midway Airport to Miami are around $59.

What is the cheapest flight available from Chicago Midway Airport?

Currently, the cheapest flight from Chicago Midway Airport found by our users is for $49 to Valparaiso, Florida. Prices will vary according to several factors such as the departure date and time, but on average you can expect to pay around $305 to travel from Chicago Midway Airport to Valparaiso, Florida.

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

Atlanta, Minneapolis and Detroit are currently the destinations served most frequently from Chicago Midway Airport, with 25, 16 and 14 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 10 as of June 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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