$43 Find Deals on Flights from 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 from Midway to Worldwide departing on 11/10. 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.
1 adult
1 adult, Economy

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Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing mié. 11/19 and returning mié. 11/26

Book Cheap International Flights from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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.

Recent round-trip international flight deals from Midway to anywhere

mié., feb. 11 - jue., feb. 19
Spirit Airlines Logo
6:00 am - 10:37 amORD-CUN
3h 37mnonstop
Spirit Airlines Logo
11:42 am - 2:50 pmCUN-ORD
4h 08mnonstop
$246Spirit Airlines
Find Deal
dom., nov. 2 - vie., nov. 7
Spirit Airlines Logo
5:10 am - 1:35 pmORD-CUN
7h 25m1 stop
Spirit Airlines Logo
2:44 pm - 12:27 amCUN-ORD
10h 43m1 stop
$247Spirit Airlines
Find Deal
mié., ene. 7 - dom., ene. 11
Spirit Airlines Logo
6:05 am - 11:00 amORD-CUN
3h 55mnonstop
Spirit Airlines Logo
11:42 am - 2:50 pmCUN-ORD
4h 08mnonstop
$248Spirit Airlines
Find Deal
mar., nov. 4 - jue., nov. 13
Delta Logo
4:56 pm - 5:05 pmORD-BCN
17h 09m2 stops
Delta Logo
10:15 am - 5:53 pmBCN-ORD
14h 38m1 stop
$453Delta
Find Deal
mié., nov. 12 - mié., nov. 19
Delta Logo
1:47 pm - 11:10 amMDW-BCN
14h 23m2 stops
Delta Logo
10:55 am - 11:40 pmBCN-MDW
19h 45m1 stop
$453Delta
Find Deal
lun., oct. 27 - mar., nov. 11
KLM Logo
1:08 pm - 7:00 amORD-BCN
11h 52m1 stop
KLM Logo
11:10 am - 8:29 pmBCN-ORD
16h 19m2 stops
$454KLM
Find Deal
mié., dic. 3 - mié., dic. 10
Delta Logo
6:00 am - 8:00 amMDW-MAD
19h 00m2 stops
Delta Logo
6:00 am - 6:00 pmMAD-MDW
19h 00m2 stops
$467Delta
Find Deal
sáb., nov. 8 - mar., nov. 25
Delta Logo
7:20 pm - 8:00 amORD-MAD
29h 40m1 stop
Delta Logo
10:00 am - 9:27 pmMAD-ORD
18h 27m2 stops
$467Delta
Find Deal
mié., dic. 3 - jue., dic. 11
Delta Logo
6:00 am - 8:00 amMDW-MAD
19h 00m2 stops
Delta Logo
1:05 pm - 11:47 pmMAD-MDW
17h 42m2 stops
$468Delta
Find Deal
jue., ene. 15 - mar., ene. 20
Multiple Airlines Logo
6:30 pm - 10:10 pmORD-BVA
20h 40m2 stops
Multiple Airlines Logo
9:00 am - 5:20 pmBVA-ORD
15h 20m2 stops
$518Multiple Airlines
Find Deal

Book Cheap Domestic Flights from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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.

Recent round-trip domestic flight deals from Midway

vie., nov. 7 - vie., nov. 7
Frontier Logo
6:15 am - 9:29 amMDW-ATL
2h 14mnonstop
Frontier Logo
9:05 pm - 10:08 pmATL-MDW
2h 03mnonstop
$84Frontier
Find Deal
mar., nov. 25 - vie., nov. 28
Frontier Logo
6:05 am - 9:22 amMDW-ATL
2h 17mnonstop
Frontier Logo
1:42 pm - 2:40 pmATL-MDW
1h 58mnonstop
$85Frontier
Find Deal
sáb., nov. 1 - dom., nov. 2
Frontier Logo
6:20 am - 9:29 amMDW-ATL
2h 09mnonstop
Frontier Logo
9:00 pm - 10:03 pmATL-MDW
2h 03mnonstop
$88Frontier
Find Deal
mié., nov. 26 - vie., nov. 28
Frontier Logo
5:30 am - 8:15 amMDW-DFW
2h 45mnonstop
Frontier Logo
10:48 pm - 1:05 amDFW-MDW
2h 17mnonstop
$93Frontier
Find Deal
lun., nov. 17 - jue., nov. 20
Frontier Logo
5:56 pm - 8:37 pmMDW-DFW
2h 41mnonstop
Frontier Logo
9:54 pm - 12:13 amDFW-MDW
2h 19mnonstop
$94Frontier
Find Deal
mié., dic. 24 - mié., dic. 31
Frontier Logo
10:21 am - 1:06 pmMDW-DFW
2h 45mnonstop
Frontier Logo
7:00 am - 9:21 amDFW-MDW
2h 21mnonstop
$95Frontier
Find Deal
sáb., oct. 25 - sáb., nov. 1
Frontier Logo
10:00 am - 5:36 pmMDW-MCO
6h 36m1 stop
Frontier Logo
8:30 am - 10:26 amMCO-MDW
2h 56mnonstop
$99Frontier
Find Deal
sáb., nov. 1 - dom., nov. 2
Frontier Logo
11:36 am - 3:16 pmMDW-MCO
2h 40mnonstop
Frontier Logo
8:59 pm - 11:30 amMCO-MDW
15h 31m1 stop
$100Frontier
Find Deal
sáb., nov. 8 - mar., nov. 11
Multiple Airlines Logo
6:15 am - 1:19 pmMDW-FLL
6h 04m1 stop
Multiple Airlines Logo
7:00 am - 11:38 amFLL-MDW
5h 38m1 stop
$122Multiple Airlines
Find Deal
mar., nov. 11 - vie., nov. 14
Southwest Logo
8:20 pm - 10:15 pmMDW-LAS
3h 55mnonstop
Southwest Logo
2:55 pm - 8:25 pmLAS-MDW
3h 30mnonstop
$141Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for flights from Midway

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

Which are the most popular places to fly to from Chicago Midway Airport?

The domestic destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.
Based on KAYAK flight searches, the most popular place to fly from Midway is New York (12% of total searches). The next most popular destinations are Dallas (8%) and Washington, D.C. (7%).

What are the most popular international flights out of Chicago Midway Airport?

The international destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.
There are many international destinations you can fly to from Chicago Midway Airport. The most popular international destinations among KAYAK users are Bangkok, Punta Cana and Tokyo.

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

There are loads of places you can fly direct to from Chicago Midway Airport. The most popular destinations for direct flights among KAYAK users are Jacksonville, Los Angeles, El Paso, Charlotte and St. Louis. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was St. Louis at $178, while the most expensive was El Paso, at $363.

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

There are many international destinations you can fly to non-stop from Chicago Midway Airport. The most popular international destinations from KAYAK users are Guadalajara, Morelia, León, Cancún and Toronto. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $199, while the most expensive was Cancún, at $315.

What is the longest direct flight from Chicago Midway Airport?

The longest direct flight you can take from Chicago Midway Airport is to San José del Cabo, with a duration of 4h 50m. The next longest is Oakland at 4h 40m, followed by a flight to San Francisco at 4h 40m.

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

The cheapest destination for a flight from Chicago found on KAYAK in the last two weeks was Atlanta and cost $34. The next cheapest destinations were New York at $36 and Louisville at $38.

Good to know

Low seasonAugust
Cheapest flight$43
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to Atlanta

FAQs for booking flights out of Chicago Midway Airport

  • Are there any airlines that operate flights from Chicago Midway International Airport (MDW) and are known for being environmentally friendly?

    If being environmentally friendly is one of your priorities, you may want to fly with Delta. Delta has a goal to replace 10% of its standard aviation fuel with sustainable aviation fuel by the end of 2030.

  • How can I go from downtown Chicago to Chicago Midway International Airport (MDW)?

    To go from downtown Chicago to Chicago Midway International Airport (MDW), you can always choose to drive, which normally takes around 20 minutes in total. Public transportation is a convenient option as well, like bus line 55, which will bring you to the airport in around 10 to 15 minutes depending on how traffic is at the time.

  • Are there any airlines that have lounges for passengers at Chicago Midway International Airport (MDW)?

    There are no airlines that currently have lounges at Chicago Midway International Airport (MDW). However, the airport does have a USO Midway Lounge, which is reserved for past and present members of the military, as well as their family members. In this lounge, travelers will have access to free snacks and drinks, as well as shower facilities.

  • What services does Chicago Midway International Airport (MDW) offer for travelers with limited mobility or disabilities?

    Chicago Midway International Airport (MDW) has wheelchairs that all guests are able to use for free. The airport also has accessible restroom stalls, elevators, and ramps that can be used to go to different floors and terminals. If you will need additional help navigating the airport, make sure to contact your airline in advance.

  • What is Midway also known as?

    Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl.

  • How does KAYAK find such low prices on flights from 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 from Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from 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 from 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 your destination with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from 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 from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight out of Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Atlanta $88 one-way - $149 round-trip; Orlando $94 one-way - $172 round-trip; Phoenix $145 one-way - $189 round-trip
  • Depending on how long your flight from Chicago Midway International Airport (MDW) will be, you may want to consider upgrading your ticket. Long-haul flights, such as those that go across the country or internationally, are often more enjoyable with extra legroom and perks. Many airlines will give you a special price to upgrade your ticket once you have made your reservation.
  • If you will be checking a substantial amount of luggage for your flight departing from Chicago Midway International Airport (MDW), you may want to consider flying with Southwest. Southwest allows all customers to check up to two bags at no additional cost.
  • Those embarking on a short flight may want to stick to bringing carry-on items. If your flight from Chicago Midway International Airport (MDW) is operated by companies such as Alaska Airlines or Delta, you will typically be able to bring one personal item and one carry-on bag for free.
  • To help save money on your flight from Chicago Midway International Airport (MDW), you may want to choose an Economy Light ticket type, rather than traditional Economy. For example, Virgin Atlantic offers these types of tickets for many of its routes.
  • For some routes that depart from Chicago Midway International Airport (MDW), you may have a layover before reaching your destination. You will find that it is quite common to change planes in cities such as Atlanta and Miami, as they are both major travel hubs.

Reviews of the top 5 airlines serving from Midway to Worldwide

 
Need help choosing which airline to fly with from Midway to Worldwide? 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.
8.0
SouthwestOverall score based on 4239 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

10.0 ExcellentAnonymous, Oct 2025BOS - BWI
Read more Southwest reviews

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

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

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

Connecting flight is on time and boarding was a breeze!

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

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.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

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.

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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