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$39 Find Cheap Flights to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap Flight Deals to Midway

 
These are the cheapest deals for flights to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from the United States to Midway.

Recent one-way flight deals to Midway

Only flying one-way? Below are some of the best one-way flight deals from the United States to Midway found on KAYAK recently.

Recent last minute flight deals to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from the United States to Midway.

Recent direct flight deals to Midway

The latest deals for direct flights from the United States to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals to Midway

Find recent round-trip train or bus tickets from the United States to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
12:57 pm - 4:06 pmMDW-ATL
2h 09mnonstop
$47Frontier
Find Deal
Wed, Nov 20 - Wed, Dec 4
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
12:09 pm - 3:23 pmMDW-ATL
2h 14mnonstop
$50Frontier
Find Deal
Wed, Nov 20 - Wed, Nov 20
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$118Southwest
Find Deal
Sat, Nov 16 - Mon, Nov 18
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
6:15 am - 9:25 amMDW-LGA
2h 10mnonstop
$133Southwest
Find Deal
Fri, Nov 15 - Sat, Nov 16
3:17 pm - 4:12 pmATL-MDW
1h 55mnonstop
6:00 am - 8:58 amMDW-ATL
1h 58mnonstop
$150Delta
Find Deal
Sat, Dec 7 - Mon, Dec 9
9:40 am - 12:33 pmEWR-MDW
3h 53m1 stop
5:59 pm - 11:07 pmMDW-EWR
4h 08m1 stop
$156Delta
Find Deal
Mon, Feb 10 - Mon, Feb 10
10:14 am - 11:29 pmEWR-MDW
14h 15m1 stop
6:17 pm - 9:19 amMDW-EWR
14h 02m1 stop
Sat, Dec 7 - Mon, Dec 9
10:14 am - 5:18 pmEWR-MDW
8h 04m1 stop
6:17 pm - 1:00 pmMDW-EWR
17h 43m1 stop
Thu, Dec 5 - Mon, Dec 9
11:15 am - 4:40 pmEWR-MDW
6h 25m1 stop
11:25 am - 6:00 pmMDW-EWR
5h 35m1 stop
$457Porter Airlines
Find Deal
Thu, Nov 28 - Thu, Dec 5
11:15 am - 4:40 pmEWR-MDW
6h 25m1 stop
11:15 am - 7:50 pmMDW-EWR
7h 35m1 stop
$462Porter Airlines
Find Deal
Thu, Dec 5 - Sun, Dec 8
2:13 pm - 3:11 pmATL-MDW
1h 58mnonstop
$39Frontier
Find Deal
Tue, Dec 31
8:23 pm - 9:29 pmATL-MDW
2h 06mnonstop
$41Frontier
Find Deal
Sun, Feb 2
2:04 pm - 4:22 pmDFW-MDW
2h 18mnonstop
$41Frontier
Find Deal
Mon, Nov 18
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
$59Southwest
Find Deal
Sat, Nov 23
10:50 am - 4:50 pmSEA-MDW
4h 00mnonstop
$69Southwest
Find Deal
Wed, Jan 8
9:40 am - 12:33 pmEWR-MDW
3h 53m1 stop
$78Delta
Find Deal
Wed, Jan 8
12:55 am - 8:50 amSEA-MDW
5h 55m1 stop
$78Delta
Find Deal
Fri, Dec 6
10:55 am - 8:04 pmEWR-MDW
10h 09m1 stop
$152Allegiant Air
Find Deal
Thu, Nov 21
10:55 am - 8:04 pmEWR-MDW
10h 09m1 stop
$183Allegiant Air
Find Deal
Thu, Nov 14
10:00 pm - 9:23 amEWR-MDW
12h 23m1 stop
$302Spirit Airlines
Find Deal
Sat, Dec 28
8:00 am - 10:23 amDFW-MDW
2h 23mnonstop
11:18 am - 2:06 pmMDW-DFW
2h 48mnonstop
$111Frontier
Find Deal
Tue, Nov 5 - Tue, Nov 12
9:40 am - 10:38 amATL-MDW
1h 58mnonstop
11:33 am - 2:45 pmMDW-ATL
2h 12mnonstop
$114Frontier
Find Deal
Tue, Nov 5 - Tue, Nov 12
9:40 am - 10:38 amDFW-MDW
24h 58m1 stop
11:59 am - 10:38 pmMDW-DFW
10h 39m1 stop
Mon, Nov 4 - Wed, Nov 6
5:30 pm - 7:30 pmDFW-MDW
26h 00m2 stops
11:33 am - 2:20 pmMDW-DFW
26h 47m1 stop
Sun, Nov 3 - Tue, Nov 5
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$278Southwest
Find Deal
Mon, Nov 4 - Mon, Nov 18
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$298Southwest
Find Deal
Tue, Nov 5 - Wed, Nov 6
12:59 pm - 5:03 pmJFK-MDW
5h 04m1 stop
5:45 pm - 11:19 pmMDW-JFK
4h 34m1 stop
$373Delta
Find Deal
Mon, Nov 4 - Sat, Nov 9
9:41 am - 7:23 pmHOU-MDW
9h 42m1 stop
11:32 am - 6:44 pmMDW-HOU
7h 12m1 stop
$375Allegiant Air
Find Deal
Fri, Nov 1 - Mon, Nov 4
6:00 am - 8:55 amEWR-MDW
3h 55m1 stop
1:30 pm - 7:35 pmMDW-EWR
5h 05m1 stop
$386Delta
Find Deal
Tue, Nov 5 - Thu, Nov 21
9:41 am - 7:23 pmHOU-MDW
9h 42m1 stop
11:32 am - 6:44 pmMDW-HOU
7h 12m1 stop
$407Allegiant Air
Find Deal
Fri, Nov 1 - Mon, Nov 4
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
12:09 pm - 3:23 pmMDW-ATL
2h 14mnonstop
$50Frontier
Find Deal
Wed, Nov 20 - Wed, Nov 20
10:58 pm - 11:55 pmATL-MDW
1h 57mnonstop
11:33 am - 2:45 pmMDW-ATL
2h 12mnonstop
$51Frontier
Find Deal
Mon, Nov 18 - Tue, Nov 19
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
9:34 am - 12:39 pmMDW-ATL
2h 05mnonstop
$52Frontier
Find Deal
Wed, Nov 20 - Tue, Dec 3
11:00 pm - 11:58 pmATL-MDW
1h 58mnonstop
12:57 pm - 4:06 pmMDW-ATL
2h 09mnonstop
$57Frontier
Find Deal
Sun, Nov 24 - Wed, Dec 4
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$118Southwest
Find Deal
Sat, Nov 16 - Mon, Nov 18
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
6:15 am - 9:25 amMDW-LGA
2h 10mnonstop
$133Southwest
Find Deal
Fri, Nov 15 - Sat, Nov 16
11:30 am - 5:35 pmSEA-MDW
4h 05mnonstop
9:15 am - 11:50 amMDW-SEA
4h 35mnonstop
$138Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
3:14 pm - 4:10 pmATL-MDW
1h 56mnonstop
6:49 pm - 9:50 pmMDW-ATL
2h 01mnonstop
$210Delta
Find Deal
Sat, Nov 16 - Mon, Nov 18
8:35 am - 9:32 amATL-MDW
1h 57mnonstop
2:38 pm - 5:31 pmMDW-ATL
1h 53mnonstop
$243Delta
Find Deal
Sat, Nov 16 - Sat, Nov 16
11:00 am - 11:58 amATL-MDW
1h 58mnonstop
4:58 pm - 7:58 pmMDW-ATL
2h 00mnonstop
$252Delta
Find Deal
Tue, Dec 10 - Tue, Dec 10
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
12:57 pm - 4:06 pmMDW-ATL
2h 09mnonstop
$47Frontier
Find Deal
Wed, Nov 20 - Wed, Dec 4
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
12:09 pm - 3:23 pmMDW-ATL
2h 14mnonstop
$50Frontier
Find Deal
Wed, Nov 20 - Wed, Nov 20
10:58 pm - 11:55 pmATL-MDW
1h 57mnonstop
11:33 am - 2:45 pmMDW-ATL
2h 12mnonstop
$51Frontier
Find Deal
Mon, Nov 18 - Tue, Nov 19
10:02 am - 11:04 amATL-MDW
2h 02mnonstop
9:34 am - 12:39 pmMDW-ATL
2h 05mnonstop
$52Frontier
Find Deal
Wed, Nov 20 - Tue, Dec 3
10:28 pm - 11:29 pmATL-MDW
2h 01mnonstop
12:57 pm - 4:06 pmMDW-ATL
2h 09mnonstop
$55Frontier
Find Deal
Sat, Dec 7 - Wed, Dec 11
11:00 pm - 11:58 pmATL-MDW
1h 58mnonstop
12:57 pm - 4:06 pmMDW-ATL
2h 09mnonstop
$57Frontier
Find Deal
Sun, Nov 24 - Wed, Dec 4
9:40 am - 10:38 amATL-MDW
1h 58mnonstop
11:33 am - 2:45 pmMDW-ATL
2h 12mnonstop
$58Frontier
Find Deal
Tue, Nov 12 - Tue, Nov 19
9:40 am - 10:38 amATL-MDW
1h 58mnonstop
12:09 pm - 3:23 pmMDW-ATL
2h 14mnonstop
$59Frontier
Find Deal
Tue, Nov 12 - Wed, Nov 20
10:59 pm - 11:56 pmATL-MDW
1h 57mnonstop
6:51 pm - 10:03 pmMDW-ATL
2h 12mnonstop
$62Frontier
Find Deal
Sat, Nov 16 - Mon, Nov 18
10:59 pm - 11:56 pmATL-MDW
1h 57mnonstop
6:51 pm - 10:03 pmMDW-ATL
2h 12mnonstop
$63Frontier
Find Deal
Sat, Nov 16 - Mon, Nov 18

Flights to Midway - Travel Insights & Trends

Get data-powered insights and trends for flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago Midway Airport?

These are the best prices found by users searching on KAYAK in the last 72 hours.
If traveling to Chicago Midway Airport, the cheapest city to fly from in the last 3 days was Atlanta, with flights as low as $39 one-way and $47 round-trip. Flights from Philadelphia are the most searched and start at $68 for a return trip.

How much is a flight to Chicago Midway Airport?

The average and cheapest price for all flights to Chicago Midway Airport from each origin found by users searching on KAYAK in the last month.
On average, a flight to Chicago Midway Airport costs $274. The cheapest price found on KAYAK in the last 2 weeks cost $35 and departed from Atlanta. The most popular routes on KAYAK are Atlanta to Chicago Midway Airport which costs $156 on average, and Philadelphia to Chicago Midway Airport, which costs $231 on average.
See prices from:

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where tickets can be as cheap as $187. On the other hand, the most expensive day to fly is Sunday, where prices are $257 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago Midway Airport is February, where tickets cost $236 on average for one-way flights. On the other hand, the most expensive months are March and December, where the average cost of tickets from the United States is $419 and $386 respectively. For return trips, the best month to travel is January with an average price of $212.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago Midway Airport is generally at night, when flights cost $210 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $297.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From New Haven $50 one-way - $130 round-trip, from Provo $67 one-way - $61 round-trip, from Los Angeles $156 one-way - $276 round-trip.

How far in advance should I book a flight to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 81 days before departure.

Good to know

Low season

January

High season

October

Cheapest flight

$39
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Atlanta to Chicago Midway Airport

When to book flights to Midway

Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago Midway Airport flights

  • Are there nonstop flights to Chicago Midway Airport from other U.S. hubs?

    Yes, there are regular nonstop flights to MDW from other U.S. hubs. If you’re on the west coast, consider nonstop flights from Los Angeles International Airport (LAX). If you’re in the southwest, nonstop flights from Dallas Fort-Worth International Airport (DFW) are an option. Those in the midwest may consider flights from St. Louis Lambert International Airport (STL). Those in the south may consider nonstop flights from Hartsfield-Jackson Atlanta International Airport (ATL). If you’re on the east coast, then consider Boston Logan International Airport (BOS).

  • What type of amenities are there for business travelers to Chicago Midway Airport?

    The business amenities at Chicago Midway Airport include free Wi-Fi all throughout the terminal so you can keep working as well as a shoe shine service in Concourse A. Furthermore, if you’d like to hold a business meeting or large convention, MDW is situated within easy access of McCormick Place, the US’s largest convention center.

  • Does Chicago Midway Airport have on-site hotels?

    Although there aren’t any on-site airport hotels at MDW, there are a few nearby hotels that you can choose from. These hotels include Holiday Inn Express & Suites, Hilton Garden Inn, DoubleTree by Hilton, and the Hyatt Place. These nearby hotels provide a free airport shuttle to pick up or drop off customers.

  • Does Chicago Midway Airport provide free parking for picking up passengers?

    Yes, Chicago Midway Airport provides free parking for family members and friends picking up passengers. This is located in the cell phone lot. It provides 90 parking spaces and is only a few mins south of the MDW entrance. Since it’s free short-term parking, drivers must attend their car at all times. When passengers are ready to leave, they may contact their friends/family members who can drive to the curbside to pick them up.

  • Which are the car rental services available at Midway Airport?

    Midway Airport has several renowned car rental companies, including National, Thrifty, Budget, Alamo, Hertz, and Enterprise. Travelers can rent their preferred vehicle from the car rental facility. A free shuttle, which stops outside the arrivals area near door 2, transports travelers from the terminal to the car rental facility.

  • Does Midway Airport have facilities for travelers with special needs and disabilities?

    Midway Airport has elevators at all levels to ensure disabled passengers can access every area of the airport. The elevators also have raised numerals and braille to ensure visually challenged travelers can use them. In addition, Travelers with special needs have designated parking spaces and are allowed to use the dedicated lanes at security. Visual paging is also available to enhance communication for deaf travelers.

  • Does Midway Airport provide departing travelers with parking facilities?

    You can leave your vehicle at the secure parking lots located near the terminal. Travelers can park at the short-term parking available at the Daily lot for around $30 per day, the Terminal Garage level 1 for approximately $64 per day or at the Economy lot for around $15 per day.

  • Can I exchange currency at Midway Airport?

    Midway Airport offers currency exchange services to travelers who want to obtain local funds. Travelers can exchange foreign currency from Seaway National Bank located in Concourse A.

  • What is the cheapest flight to Chicago Midway Airport?

    If traveling to Chicago Midway Airport, the cheapest city to fly from in the last 3 days was Atlanta, with flights as low as $39 one-way and $47 round-trip. Flights from Philadelphia are the most searched and start at $68 for a return trip.

  • How far is Chicago Midway Airport from central Chicago?

    There are 9 miles between Chicago city center and Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $274. The cheapest price found on KAYAK in the last 2 weeks cost $35 and departed from Atlanta Hartsfield-Jackson Airport.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.
  • Do you have some extra time to spare while at Chicago Midway Airport? If so, why not check out the multiple art exhibitions that they have throughout the airport. These include the Dauntless Dive Bomber in Concourse A, the murals in baggage claim, and the murals in the CTA pedestrian corridor.
  • Do you have a service animal or emotional support animal while at Chicago Midway Airport? If so, rest assured that there are pet relief areas inside of MDW. These include one nearby Gate A4A and one outside of baggage claim near Door 4.
  • Is your luggage weighing you down while at Chicago Midway Airport? If so, keep an eye out for the luggage cars at the entrance and exits of the baggage claim area. They're available for a small fee.
  • If your phone’s battery is getting low while at Chicago Midway Airport, rest assured that MDW provides multiple workstations with power outlets throughout the seating areas. On top of that, most seats in the gated areas are equipped with outlets as well.
  • Do you need a moment of quiet to pray while at Chicago Midway Airport? If so, consider heading to the Chapel. It’s located on the Mezzanine level of Concourse C right above the food court.
  • The most economical transportation means from Midway Airport (MDW) to downtown Chicago are the CTA trains, which travelers can board from the airport at the CTA orange line station. The train takes around 25min to get to the city and charges around $2.50. If you take a taxi from the airport, it will take you around 15min to reach the city. Taxis charge around $25 for a one-way trip.
  • Active members of the military and their families traveling through Midway Airport can enjoy the facilities at the cozy USO lounge as they wait for their flights. The lounge, which military members can access free of charge, is located in Concourse C.
  • If you are traveling through Midway Airport with young children, you can use the designated family lane to get you through security quicker. Travelers with infants can also utilize the baby changing facilities in the airport’s restrooms.
  • If you and your kids need to grab a bite before your flight, Midway Airport has several family-friendly restaurants located on the airside.
  • If you feel overwhelmed by the stress of travel, you can squeeze in some relaxation time and a good workout at the yoga room. The airport’s yoga room, located in Concourse C, comes equipped with a TV displaying yoga exercises, which you can follow.
  • Southwest Airlines offers nonstop flights from Midway Airport to Atlanta, while some major airlines like Delta Air Lines have a changeover at Detroit before landing in Atlanta.
  • You should fly into Midway Airport if you are traveling to Summit, located approximately 3 miles away, Bridgeview, located approximately 4.27 miles away, or Lyons, situated approximately 3.9 miles away from the airport.
See more tips

Flights to Midway: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Midway 
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.
Verified travelerFlew with FrontierDFW-MDWDec 2023
Don’t take advantage of your customers to meet a quota.

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Chicago Midway Airport, which days they fly and book direct flights.

Nonstop departures

United States to Chicago Midway

Monday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Tuesday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Wednesday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Thursday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Friday

Aeromexico, Air France, Air Transat, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Air Transat, +11 more

Aeromexico, Air France, +12 more

Sunday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

See more direct flights

Nonstop returns

Chicago Midway to United States

Monday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Tuesday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Wednesday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Thursday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Friday

Aeromexico, Air France, Air Transat, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Air Transat, +11 more

Aeromexico, Air France, +12 more

Sunday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

See more direct flights
See more direct flights

Top 5 airlines flying to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the United States to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 5116 reviews
8.1Comfort
8.7Crew
7.7Entertainment
8.3Boarding
7.2Food
Airline reviews

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

6.0 GoodJames, Oct 2024DEN - AUS
Read more Southwest reviews

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

The fluidity of the entire process of boarding the plane the flight attendants attentiveness. The flight attendants also provided coloring books for my kids who loved it.

I used to fly SWA all the time. I know the crew has their little acts that are often fun, and entertaining. On this flight one of the crew was just not nice. Very surprising.

It was really nice! I appreciate the gate attendant allowing families with small children to board early on in the process… that was very helpful! The internet service didn’t work with the app I was trying to use even though I paid the $8… other than that it was great! Oh and I should’ve asked for the whole cranberry cocktail can. That cup was about 2 sips…

Delayed 4 hours due to mechanical issues. No mention of compensation for being over 3 hours late

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Flight did not have seat back entertainment and the wifi was iffy.

Pretty standard flight. Delta has a good selection of movies.

The WiFi has been awful on my last few Delta Air Lines flights.

The seats are uncomfortable, feels like a small seat pad on plywood.

The seats are uncomfortable and there was no power to recharge a phone.

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

Some sort of compensation for missing work because of a cancelled flight that was United’s fault

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

I went to the Frontier counter in San Jose at 1030am or so on Sunday 10/13/24 to see if I could get an earlier flight to San Diego in lieu of my reserved 630pm flight. One thing led to another, and I was able to obtain an open seat for about $ 56. on the earlier flight. Fine. Then the agent asked if I "was checking a bag". Not knowing that carry-ons cost extra per Frontier policy, I thought that she meant a regular checked bag. Therefore, I said no. Once I got to the gate, the same gate agent who sold me a ticket told me that I had to pay $99 for a carry-on, and that all bags were extra on Frontier. Having never flown on Frontier, I was not aware of this. Part of the issue was that she was not a native English speaker, so there was a miscommunication as to what "bag" meant. I would have preferred for her to have clearly let me know at the front counter that any bag including a carry-on cost $99. It would have had the same outcome, as I had to take my carry-on. But it got hectic at the last minute at the gate itself. The baggage policy should have mentioned "including carry-ons" when we first spoke.

Book Cheap Chicago Plane Tickets

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
11/20Wed
nonstopFrontier
2h 02mATL-MDW
12/4Wed
nonstopFrontier
2h 09mMDW-ATL
$47
11/20Wed
nonstopFrontier
2h 02mATL-MDW
11/20Wed
nonstopFrontier
2h 14mMDW-ATL
$50
11/16Sat
nonstopSouthwest
2h 30mLGA-MDW
11/18Mon
nonstopSouthwest
2h 05mMDW-LGA
$118
11/15Fri
nonstopSouthwest
2h 25mLGA-MDW
11/16Sat
nonstopSouthwest
2h 10mMDW-LGA
$133
12/7Sat
nonstopDelta
1h 55mATL-MDW
12/9Mon
nonstopDelta
1h 58mMDW-ATL
$150
2/10Mon
1 stopDelta
3h 53mEWR-MDW
2/10Mon
1 stopDelta
4h 08mMDW-EWR
$156
12/7Sat
1 stop
14h 15mEWR-MDW
12/9Mon
1 stop
14h 02mMDW-EWR
$167
12/5Thu
1 stop
8h 04mEWR-MDW
12/9Mon
1 stop
17h 43mMDW-EWR
$186
11/28Thu
1 stopPorter Airlines
6h 25mEWR-MDW
12/5Thu
1 stopPorter Airlines
5h 35mMDW-EWR
$457
12/5Thu
1 stopPorter Airlines
6h 25mEWR-MDW
12/8Sun
1 stopPorter Airlines
7h 35mMDW-EWR
$462

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
12/31Tue
nonstopFrontier
1h 58mATL-MDW
$39
2/2Sun
nonstopFrontier
2h 06mATL-MDW
$41
11/18Mon
nonstopFrontier
2h 18mDFW-MDW
$41
11/23Sat
nonstopSouthwest
2h 25mLGA-MDW
$59
1/8Wed
nonstopSouthwest
4h 00mSEA-MDW
$69
1/8Wed
1 stopDelta
3h 53mEWR-MDW
$78
12/6Fri
1 stopDelta
5h 55mSEA-MDW
$78
11/21Thu
1 stopAllegiant Air
10h 09mEWR-MDW
$152
11/14Thu
1 stopAllegiant Air
10h 09mEWR-MDW
$183
12/28Sat
1 stopSpirit Airlines
12h 23mEWR-MDW
$302

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Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
11/5Tue
nonstopFrontier
2h 23mDFW-MDW
11/12Tue
nonstopFrontier
2h 48mMDW-DFW
$111
11/5Tue
nonstopFrontier
1h 58mATL-MDW
11/12Tue
nonstopFrontier
2h 12mMDW-ATL
$114
11/4Mon
multi-stop
24h 58mDFW-MDW
11/6Wed
multi-stop
10h 39mMDW-DFW
$242
11/3Sun
multi-stop
26h 00mDFW-MDW
11/5Tue
multi-stop
26h 47mMDW-DFW
$257
11/4Mon
nonstopSouthwest
2h 25mLGA-MDW
11/18Mon
nonstopSouthwest
2h 05mMDW-LGA
$278
11/5Tue
nonstopSouthwest
2h 25mLGA-MDW
11/6Wed
nonstopSouthwest
2h 05mMDW-LGA
$298
11/4Mon
multi-stopDelta
5h 04mJFK-MDW
11/9Sat
multi-stopDelta
4h 34mMDW-JFK
$373
11/1Fri
multi-stopAllegiant Air
9h 42mHOU-MDW
11/4Mon
multi-stopAllegiant Air
7h 12mMDW-HOU
$375
11/5Tue
multi-stopDelta
3h 55mEWR-MDW
11/21Thu
multi-stopDelta
5h 05mMDW-EWR
$386
11/1Fri
multi-stopAllegiant Air
9h 42mHOU-MDW
11/4Mon
multi-stopAllegiant Air
7h 12mMDW-HOU
$407

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Everything you need to know for your flight to Midway

Flights with popular airlines flying to Chicago

Flight deals from the most popular airlines with KAYAK users flying the route