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Midway

$83+ Cheap flights from Chicago Midway Airport

MDW — EWR
Nov 18 — Nov 251
Wed 11/18
Wed 11/25
1 adult, Economy
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Find flights from Midway within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAtlanta

MDW Chicago Midway - ATL Atlanta Hartsfield-Jackson

MDWATL

Chicago Midway

Wed 11/11

1:30 pm-8:40 pm

1 stop6h 10m

Atlanta Hartsfield-Jackson

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$108

ChicagoAtlanta

MDW Chicago Midway - ATL Atlanta Hartsfield-Jackson

MDWATL

Chicago Midway

Sat 1/9

2:10 pm-8:05 pm

1 stop4h 55m

Atlanta Hartsfield-Jackson

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$109

ChicagoAtlanta

MDW Chicago Midway - ATL Atlanta Hartsfield-Jackson

MDWATL

Chicago Midway

Tue 1/12

1:40 pm-8:40 pm

1 stop6h 00m

Atlanta Hartsfield-Jackson

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$109

ChicagoAtlanta

MDW Chicago Midway - ATL Atlanta Hartsfield-Jackson

MDWATL

Chicago Midway

Sat 12/12

8:00 am-4:45 pm

2 stops7h 45m

Atlanta Hartsfield-Jackson

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$114

ChicagoDenver

MDW Chicago Midway - DEN Denver Intl

MDWDEN

Chicago Midway

Sat 12/5

11:05 am-5:40 pm

2 stops7h 35m

Denver Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$115

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Wed 12/2

7:35 am-5:10 pm

2 stops8h 35m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$116

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Mon 12/21

8:00 am-1:50 pm

1 stop4h 50m

Boston Logan Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$117

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Sat 12/19

8:50 pm-12:30 am

Nonstop2h 40m

Orlando

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$117

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Wed 1/6

1:25 pm-5:00 pm

Nonstop2h 35m

Orlando

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$117

ChicagoOrlando

MDW Chicago Midway - MCO Orlando

MDWMCO

Chicago Midway

Sat 12/5

6:30 pm-10:10 pm

Nonstop2h 40m

Orlando

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Midway

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway in October
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: Among all the travel providers offering deals on flights from Chicago Midway Airport, FlightHub has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as FlightHub about >95% of the time. This is based on searches for flights from Chicago Midway Airport made on Cheapflights over the past month and is updated monthly.
  • Most trusted provider: In terms of trustworthiness, Cheapflights users rate FlightHub the highest out of those offering flight deals from Chicago Midway Airport. FlightHub has a user feedback rating of 3 out of 3 stars (3 being the best) and has received the most positive sentiment from Cheapflights users searching for flights from Chicago Midway Airport. This info is gathered from Cheapflights searches over the past month.

Midway travel tips

  • When traveling through the Chicago Midway International Airport (MDW), note that the security checkpoint offers three different lanes for your convenience: a business/experienced traveler lane, a lane for casual travelers, and a family lane for travelers with children who may need additional time to go at their own pace.
  • Travelers to Chicago Midway International Airport (MDW) in need of translation services are encouraged to seek out the information book in the baggage claim area of the terminal. There they will find I-Speak language cards and a Limited English Proficiency phone, which offers a quick, convenient connection to quality interpreters who speak over 200 different languages.
  • If traveling internationally from the Chicago Midway International Airport (MDW), note that the airport’s on-site Seaway National Bank offers exchange services for converting your money into foreign currency. More than 200 currencies may be bought and sold at this location. For even faster service, you may call in your exchange ahead of your arrival.

Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated round-trip price

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago Midway Airport?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport (average of $102). Flying from Chicago Midway Airport in July will prove the most costly (average of $386). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago Midway Airport?

For flights departing from Chicago Midway Airport check dates and pricing for the following: Frontier, Delta. These airlines depart to the following popular destinations: New York.

Southwest
Southwest
From $97
Frontier
Frontier
From $56
Volaris
Volaris
From $206
Delta
Delta
From $88

What are popular destinations to fly to from Chicago Midway Airport?

Some of the most frequent flights departing from Chicago Midway Airport everyday are: Detroit (162 flights per day), Atlanta (113 flights per day), and Orlando (86 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $84
Dallas/Fort Worth
Dallas/Fort Worth
From $90
Orlando
Orlando
From $129
New York
New York
From $98

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Valparaiso Destin-Ft Walton Beach, with prices starting at $53. Explore other affordable destinations below.

Valparaiso Destin-Ft Walton Beach
Valparaiso Destin-Ft Walton Beach
From $53
Knoxville McGhee Tyson
Knoxville McGhee Tyson
From $57
Minneapolis St Paul
Minneapolis St Paul
From $58
Fort Lauderdale
Fort Lauderdale
From $61

Airline reviews for flights from Midway

Read through reviews of airlines servicing Chicago Midway Airport, such as Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,649 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
Delta
7.8
Good
8,649 reviews
Delta
7.8
Good
8,649 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
Frontier
5.5
Fair
2,525 reviews
Delta
7.8
Good
8,649 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Atlanta, Las Vegas, Dallas/Fort Worth Airport. Throughout the year, Atlanta, Orlando Airport, Las Vegas are some of the top choices made by users flying from Chicago Midway Airport.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as $53 to Valparaiso, Florida (prices may vary depending on the airline and departure time). On average, users have booked flights for $379 to fly from Chicago Midway Airport.

  • What are the cheapest airlines flying from Chicago Midway Airport to anywhere?

    Over the past few days, we've found that Frontier, Porter Airlines, and Allegiant Air have the cheapest prices from Chicago Midway Airport. Frontier flights from Chicago Midway Airport to Atlanta Hartsfield-Jackson ($56), Porter Airlines flights from Chicago Midway Airport to Montreal ($69), and Allegiant Air flights from Chicago Midway Airport to Asheville Regional ($82).

  • What is the cheapest premium economy flight from Chicago Midway Airport?

    Options for some of the cheapest premium economy flights from Chicago Midway Airport we have found on Cheapflights are as follows:
    Fly from Chicago Midway to Newark Airport starting at $54
    Fly from Chicago Midway to Orlando Airport starting at $187
    Fly from Chicago Midway to Cancún starting at $404
    Fly from Chicago Midway to Miami starting at $405

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

    If you’re looking for a cheap first-class flight from Chicago Midway Airport, consider Minneapolis. Prices start at $546 so you can fly first-class even on a budget.

  • What is the cheapest month to fly from Chicago Midway Airport?

    March is currently the cheapest month to fly from Chicago Midway Airport. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    Check out the cheapest flights from Chicago Midway Airport to embark to:
    Fly from Chicago to Dallas from $52 round trip
    Fly from Chicago to Valparaiso from $79 round trip
    Fly from Chicago to Knoxville from $86 round trip
    Fly from Chicago to Minneapolis from $117 round trip
    Fly from Chicago to Memphis from $117 round trip

  • Does the Chicago Midway International Airport (MDW) offer on-site accommodations?

    While the Chicago Midway International Airport (MDW) does not offer an on-site hotel at this time, there are ample accommodations available within a handful of miles to choose from, including The Courtyard by Marriot, which is only 9 minutes away.

  • What amenities are available at the Chicago Midway International Airport (MDW) for nursing mothers?

    The Chicago Midway International Airport (MDW) offers a Mother’s Room, which features a comfortable seating area, sink and wash area, and wall-mounted TV in a private setting. Additionally, lactation pods throughout the airport provide safe and private spaces for mothers to nurse or pump while traveling.

  • Does the Chicago Midway International Airport (MDW) offer quiet spaces for those looking to escape the excitement of a travel hub??

    Yes, in Concourse C of the Chicago Midway International Airport (MDW) you will find a Yoga Room, which offers passengers a place to retreat and meditate between the hours of 6 am and 10 pm.

  • Are there shopping opportunities available at the Chicago Midway International Airport (MDW)?

    Yes, the Chicago Midway International Airport (MDW) offers a wide variety of shopping options, from convenience stores and kiosks to popular companies like Build-A-Bear Workshop to smaller retailers offering unique, local souvenirs and gifts.

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