Is Southwest the cheapest airline to fly with from Baltimore to Chicago Midway Airport?

With an average price of $296 return, Southwest is not the cheapest airline to fly from Baltimore to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $167 on average.

Does Southwest fly direct to Chicago Midway Airport from Baltimore?

Yes, Southwest does offer direct flights for the route, with around 45 flights per week.

What’s the cheapest day of the week to fly from Baltimore to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from Baltimore to Chicago Midway Airport with Southwest is Thursday, when prices are around $63. The most expensive day is generally Saturday, where the average price is around $144.

What’s the cheapest month to fly from Baltimore to Chicago Midway Airport with Southwest?

The cheapest month for Southwest flights to Chicago Midway Airport from Baltimore is generally September, where plane tickets cost $88 on average. If possible, try to avoid the most expensive months of April and July, where tickets cost $359 and $359 respectively.

$70 Cheap Southwest Flights from Baltimore to Chicago Midway Airport

BWI - MDW

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Flight Deals

Cheap Southwest Flight Deals from Baltimore to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Baltimore to Chicago Midway Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Baltimore to Chicago Midway Airport

Wed, Nov 12 - Sat, Nov 15

4:45 pm - 5:50 pmBWI-MDW

2h 05mnonstop

4:45 pm - 7:35 pmMDW-BWI

1h 50mnonstop

$139Southwest

Find Deal

Mon, Nov 24 - Thu, Nov 27

6:20 pm - 8:40 pmBWI-MDW

3h 20m1 stop

2:30 pm - 5:15 pmMDW-BWI

1h 45mnonstop

$149Southwest

Find Deal

Sat, Dec 6 - Mon, Dec 8

5:20 pm - 6:30 pmBWI-MDW

2h 10mnonstop

9:20 am - 12:10 pmMDW-BWI

1h 50mnonstop

$158Southwest

Find Deal

Sat, Nov 1 - Tue, Nov 4

8:00 pm - 9:00 pmBWI-MDW

2h 00mnonstop

6:55 pm - 9:45 pmMDW-BWI

1h 50mnonstop

$159Southwest

Find Deal

Fri, Dec 12 - Sun, Dec 14

7:30 pm - 8:40 pmBWI-MDW

2h 10mnonstop

5:05 am - 7:55 amMDW-BWI

1h 50mnonstop

$177Southwest

Find Deal

Fri, Nov 14 - Sat, Nov 15

9:55 pm - 11:00 pmBWI-MDW

2h 05mnonstop

6:40 am - 9:30 amMDW-BWI

1h 50mnonstop

$178Southwest

Find Deal

Wed, Nov 12 - Sat, Nov 15

2:25 pm - 5:35 pmBWI-MDW

4h 10m1 stop

4:45 pm - 7:35 pmMDW-BWI

1h 50mnonstop

$180Southwest

Find Deal

Sat, Dec 6 - Mon, Dec 8

5:20 pm - 6:30 pmBWI-MDW

2h 10mnonstop

1:45 pm - 7:50 pmMDW-BWI

5h 05m1 stop

$184Southwest

Find Deal

Sat, Nov 1 - Mon, Nov 3

2:30 pm - 3:30 pmBWI-MDW

2h 00mnonstop

6:40 am - 9:30 amMDW-BWI

1h 50mnonstop

$188Southwest

Find Deal

Sat, Nov 1 - Tue, Nov 4

8:00 pm - 9:00 pmBWI-MDW

2h 00mnonstop

2:30 pm - 7:30 pmMDW-BWI

4h 00m1 stop

$190Southwest

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Useful Info

Low season	January
High season	October
Cheapest flight	$70
Average price round-trip	$212

Best time to beat the crowds with an average 0% drop in price.

Most popular time to fly and prices are also 10% lower on average.

Flight from Baltimore to Chicago Midway Airport

(price for this month)

When to Book Flights with Southwest from Baltimore to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Baltimore to Chicago Midway Airport?
With an average price of $296 return, Southwest is not the cheapest airline to fly from Baltimore to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $167 on average.
What is the cheapest Southwest flight from Baltimore to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from Baltimore to Chicago Midway Airport was $107 for a return flight and $51 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from Baltimore?
Yes, Southwest does offer direct flights for the route, with around 45 flights per week.
What’s the cheapest day of the week to fly from Baltimore to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from Baltimore to Chicago Midway Airport with Southwest is Thursday, when prices are around $63. The most expensive day is generally Saturday, where the average price is around $144.
What’s the cheapest month to fly from Baltimore to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from Baltimore is generally September, where plane tickets cost $88 on average. If possible, try to avoid the most expensive months of April and July, where tickets cost $359 and $359 respectively.

8.0

Very good4,235 verified ratings

8.0Comfort

8.6Crew

8.1Boarding

7.5Entertainment

7.0Food

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

Aleksandar, Oct 2025

OAK-SAN

On time, and it was not full flight

4.0 Mediocre

Annette, Oct 2025

LGA-MCI

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

10.0 Wonderful

Gerald, Oct 2025

SJC-PDX

Boarding quick & efficient. Crew was friendly. Arrived early

6.0 Okay

Hung, Oct 2025

PHX-ABQ

mandatory demand customer to check their carry on because not enough people check bags.

8.0 Very good

Annette, Oct 2025

MCI-LGA

Good non stop is always good

10.0 Wonderful

Gabriel, Sep 2025

DEN-SMF

Connecting flight is on time and boarding was a breeze!

10.0 Wonderful

Gabriel, Sep 2025

LGA-DEN

Easy boarding process. No delays!

10.0 Wonderful

Melissa, Sep 2025

MDW-DTW

Excellent

10.0 Wonderful

Melissa, Sep 2025

MSY-MDW

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 Wonderful

Robert, Sep 2025

RNO-LAS

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

Everything you need to know for your flight from Baltimore to Chicago Midway Airport

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Cabin class types available on flights to Chicago Midway Airport

First Class flights from Baltimore to Chicago Midway Airport

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BWI - MDW

$70 Find Cheap Southwest Flights from Baltimore to Chicago Midway Airport

Search hundreds of travel sites at once for deals on Southwest flights from Baltimore to Chicago Midway Airport

Cheap Southwest Flight Deals from Baltimore to Chicago Midway Airport

Recent round-trip Southwest flight deals from Baltimore to Chicago Midway Airport

Recent one-way Southwest flight deals from Baltimore to Chicago Midway Airport

Recent last minute Southwest flight deals from Baltimore to Chicago Midway Airport

Recent direct Southwest flight deals from Baltimore to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from Baltimore to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

Is Southwest the cheapest airline to fly with from Baltimore to Chicago Midway Airport?

What is the cheapest Southwest flight from Baltimore to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from Baltimore?

What’s the cheapest day of the week to fly from Baltimore to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from Baltimore to Chicago Midway Airport with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Baltimore to Chicago Midway Airport

Cabin class types available on flights to Chicago Midway Airport

Cabin classes available on flights to Baltimore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Chicago Midway Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.