$30 Find Cheap Flights from Chicago Midway Airport to North America

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 North America departing on 7/29. 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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1 adult, Economy

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Best North America Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New York1 stop$105
Los Angeles
Los Angeles1 stop$121
Orlando
Orlandononstop$94
Las Vegas
Las Vegas1 stop$111
Miami
Miaminonstop$88
San Francisco
San Francisco1 stop$121
Boston
Bostonnonstop$137
Washington, D.C.
Baltimorenonstop$77
Denver
Denvernonstop$97
Seattle
Seattle1 stop$143
Fort Lauderdale
Fort Lauderdale1 stop$110
Atlanta
Atlantanonstop$69
Dallas
Dallasnonstop$74
Tampa
Tampanonstop$87
Houston
Houstonnonstop$92
Cancún
Cancúnnonstop$269
Honolulu
Honolulu1 stop$465
San Diego
San Diego1 stop$121
New York
New York1 stop$105
Los Angeles
Los Angeles1 stop$121
Orlando
Orlandononstop$94
Las Vegas
Las Vegas1 stop$111
Miami
Miaminonstop$88
San Francisco
San Francisco1 stop$121
Boston
Bostonnonstop$137
Washington, D.C.
Baltimorenonstop$77
Denver
Denvernonstop$97
Seattle
Seattle1 stop$143
Fort Lauderdale
Fort Lauderdale1 stop$110
Atlanta
Atlantanonstop$69
Dallas
Dallasnonstop$74
Tampa
Tampanonstop$87
Houston
Houstonnonstop$92
Cancún
Cancúnnonstop$269
Honolulu
Honolulu1 stop$465
San Diego
San Diego1 stop$121

Cheap Flights from Midway to North America

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

Tue, Jul 29 - Tue, Aug 5
Frontier Logo
11:39 am - 2:45 pmMDW-ATL
2h 06mnonstop
Frontier Logo
9:37 am - 10:40 amATL-MDW
2h 03mnonstop
$69Frontier
Find Deal
Tue, Jul 29 - Tue, Aug 5
Frontier Logo
11:39 am - 2:45 pmMDW-ATL
2h 06mnonstop
Frontier Logo
9:37 am - 10:40 amATL-MDW
2h 03mnonstop
$70Frontier
Find Deal
Wed, Sep 3 - Wed, Sep 3
Southwest Logo
6:00 am - 9:00 amMDW-LGA
2h 00mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$137Southwest
Find Deal
Sat, Sep 13 - Wed, Sep 17
Southwest Logo
6:55 am - 9:55 amMDW-LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
$147Southwest
Find Deal
Mon, Sep 22 - Fri, Sep 26
 Logo
4:48 pm - 8:21 pmMDW-LAS
5h 33m1 stop
 Logo
3:22 pm - 8:52 pmLAS-MDW
3h 30mnonstop
Sat, Sep 20 - Wed, Sep 24
Delta Logo
6:00 am - 2:20 pmMDW-EWR
7h 20m1 stop
Delta Logo
3:29 pm - 9:36 pmEWR-MDW
7h 07m1 stop
$177Delta
Find Deal
Wed, Sep 3 - Wed, Sep 10
Delta Logo
6:00 am - 12:11 pmMDW-EWR
5h 11m1 stop
Delta Logo
1:00 pm - 6:37 pmEWR-MDW
6h 37m1 stop
$178Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Aeromexico Logo
10:31 am - 8:20 pmMDW-CUN
9h 49m1 stop
Aeromexico Logo
8:00 am - 9:12 pmCUN-MDW
13h 12m1 stop
$304Aeromexico
Find Deal
Fri, Sep 5 - Sat, Sep 6
Aeromexico Logo
6:00 am - 7:40 pmMDW-MEX
14h 40m1 stop
Aeromexico Logo
7:10 am - 9:12 pmMEX-MDW
13h 02m2 stops
$310Aeromexico
Find Deal
Thu, Aug 21 - Sun, Aug 24
 Logo
3:52 pm - 10:55 pmMDW-MEX
8h 03m1 stop
 Logo
6:20 am - 1:56 pmMEX-MDW
6h 36m1 stop
Useful Info

KAYAK's insights & trends for Midway to North America flights

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

What is the cheapest Chicago Midway Airport to North America flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to North America.

The cheapest ticket to North America from Chicago Midway Airport found in the last 72 hours was to Atlanta, at $113 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Atlanta (ATL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $113.

Can I save money by flying with a layover from Chicago Midway Airport to North America?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to North America, 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 from Chicago Midway Airport to North America is September, when tickets cost $207 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $379 and $307 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to North America?

The average price of all round-trip flights from Chicago Midway Airport to North America clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to North America on a Saturday and more expensive on a Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$30
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago Midway Airport to Atlanta

FAQs - booking North America flights

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

    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 to North America.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to North America 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 to North America?

    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 from Chicago Midway Airport to North America 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 from Chicago Midway Airport to North America?

    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 to North America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to North America?

    The cheapest time of day to fly to North America is generally at night, when round-trip flights cost $238 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to North America is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $268.

Top tips for finding cheap flights to North America

  • 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 $119 one-way - $196 round-trip; Denver $125 one-way - $184 round-trip; Orlando $112 one-way - $222 round-trip

Reviews of the top 5 airlines serving from Midway to North America

 
Need help choosing which airline to fly with from Midway to North America? 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 4272 reviews
7.0Food
8.0Comfort
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

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.

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.

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.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

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