How long does a flight from St. John's to Chicago take?

There are no direct flights from St. John's to Chicago. The quickest journey takes 11h 17m. Visit our flight page for the latest deals!

Do I need a passport to fly between St. John's and Chicago?

Yes Visit our flight page for the latest deals!

What’s the cheapest day of the week to fly from St. John's to Chicago?

If you are looking for a flight deal from St. John's to Chicago, look for departures on Wednesdays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago, Tuesday is the cheapest day to fly and Sunday is the most expensive. Visit our flight page for the latest deals!

Which airports will I be using when flying from St. John's to Chicago?

On your way to Chicago, you’ll fly out from YYT. You’ll be landing at MDW. Visit our flight page for the latest deals!

What’s the earliest departure time from St. John's to Chicago?

The earliest departure to Chicago leaves St. John's at 2:30 am.

What’s the latest departure time from St. John's to Chicago?

The last departure to Chicago leaves St. John's at 12:15 pm.

Which airlines fly nonstop between St. John's and Chicago?

There are no direct flights connecting St. John's to Chicago.

Which aircraft models fly most regularly from St. John's to Chicago?

We unfortunately don’t have that data for this specific route.

How does KAYAK find such low prices on flights from St. John's to Chicago?

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 St. John's to Chicago. Visit our flight page for the latest deals!

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from St. John's to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from St. John's is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!

What is the Hacker Fare option on flights from St. John's to Chicago?

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 with an airline and back to St. John's with another airline. Booking your flights between St. John's and MDW can sometimes prove cheaper using this method. Visit our flight page for the latest deals!

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from St. John's to Chicago?

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 from St. John's up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!

YYT - MDW

Find cheap flights from St. John's to Chicago from $491

Here is why travelers choose KAYAK

Save 22% or moreCompare multiple travel sites with one search

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

When to book flights from St. John's to Midway

Estimated round-trip price

Average price per month

Flight prices as travel date approaches

7.7

Porter AirlinesOverall score based on 2704 reviews

7.8Boarding

7.8Comfort

8.3Crew

6.8Entertainment

7.8Food

Airline reviews

Pros: "Nothing"

Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."

Read more about Porter Airlines

Pros: "Nothing"

Pros: "Efficient check in. Liked the shuttle bus service from subway to airport."

Cons: "As expected this is a commuter flight so very stripped down in terms of amenities. Tight plane seating and those overhead bins just barely accommodate the carry on."

Pros: "The crew was helpful and everything was on time."

Cons: "The ride was a bit rough at the end if the flight."

Pros: "Friendly crew"

Cons: "All good"

Pros: "The crew is lovely"

Cons: "Porters flights out of Toronto have been significantly delayed every time I’ve flown"

Pros: "Seamless checkin and boarding. Captain got us home 20mins early. Love Porter!"

Cons: "I wish the airplane had USB plugs to charge my phone. Maybe one day Porter will retrofit the airplanes with more conveniences."

Cons: "Flight was delayed"

Pros: "N/A"

Cons: "Same as previous answer, but due to cancellation of earlier flight and our connection being delayed, ended up not landing in Newark until about 10pm when we originally should've landed in around 3. This caused us to miss a Broadway show we had bought tickets for ($150/ticket) as well as lost out on dinner reservations we had made. We then had to take an Uber as our friends could not pick us up at that time (a further $80). My son had taken off three days from work and we lost most of the first one due to Porter's incompetence. Their only comment was that they weren't obliged to do anything for us because we had booked through an agent and not directly with Porter."

Pros: "All ok"

Cons: "Not a thing"

Pros: "We waited 45min in the plane before taking off, I missed my transfert flight and I had to wait for the next one in Toronto"

Pros: "Fast and convenient"

Pros: "First time in 10 flights in 3 months flying with Porter in time - what a miracle!"

Pros: "Free bar nuts while delayed 10 hours"

Cons: "Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be"

Pros: "Once we got on the flight it was fine."

Cons: "Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages."

Pros: "It was hassle free. Trace and arrival times were perfect. Thank you for caring."

Cons: "Got to Billy Bishop, only to find out flight is delayed 2 hours."

Pros: "Convenient, easy boarding, snacks and free wine on leg from toronto to chicago"

Pros: "The check in process was very easy. The boarding process was very easy. The flight attendants were very pleasant."

Cons: "There was not anything to complain about."

Pros: "the flight itself was good. the price was also good."

Cons: "delay of 1hour for both flights."

Cons: "Major delays that were poorly handled."

Cons: "Delay"

Pros: "The flight attendants were very nice and helpful"

Cons: "The flight was delayed"

Pros: "fast"

Cons: "no TSA precheck"

Pros: "I liked the lounge"

Cons: "There were a lot of people and not enough outlets"

Cons: "Good"

Pros: "The flight was early!"

Cons: "It was uncomfortable because the flight was so long, and I couldn't stretch out very much"

Pros: "Nothing"

Cons: "Everything"

Pros: "Onboard crew was very nice"

Cons: "Crew didn't answer any of my questions, were snappy, and rude."

Pros: "Polite crew"

Cons: "Would like a sandwich instead of nuts"

Pros: "Efficient"

Cons: "Late flight"

Pros: "Everything"

Cons: "Nothing"

Pros: "Crew was very friendly and sincere."

Cons: "Delayedx3."

Pros: "On time, no issues, good staff"

Pros: "Although our flight was delayed about 40 mins., the lounge was comfortable and with privacy between seating areas. There was also complimentary coffee, tea, water and cookies. Boarding was quick and easy and the flight was comfortable."

Cons: "If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems."

Pros: "Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight."

Cons: "Louder than a usual commercial flight, probably due to being a turboprop aircraft."

Pros: "There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays."

Pros: "It was on time"

Cons: "We had to make a second pass at Halifax due to a glitch"

Pros: "Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter."

Pros: "Breakfast, bars, etcnithin"

Cons: "Nada"

Pros: "Lounge with free drinks (soda, coffee, water) and cookies/snacks! Glass drinks glasses on the plane! And leg room!"

Pros: "Real glasses on the plane that was nice"

Cons: "Well first they rebooked me due to weather from Quebec City to Toronto, but had no ability to print me a boarding pass. So I had to wait in line in Toronto for a bairisng pass only to realize she printed out a boarding pass for my ORIGINAL flight. When I asked the agent about it, she said "oh, well you better run to catch is then." WTF! First time on Porter and never again. They're supposed to be some sort of luxury experience which is laughable."

Cons: "I fly weekly for work, but last week I got to fly to Toronto for pleasure to see my fiancé. In all of my years of traveling, I have missed a flight maybe 5 times due to traffic, weather, or other uncontrollable factors. It happened to be that on my way to Chicago Midway, there was an accident on the road that stopped traffic dead for 40 minutes. When I arrived at the airport, I begged for people to help me out by letting me cut security lines so that I wouldn't be late, but alas...others were also rushed and the TSA agents weren't too helpful. I arrived at the gate for my flight about 3 minutes late in defeat. Oh well - it happens! What was really unpleasant was that nobody would help me out. I was charged $150 to "change" my flight instead of just getting rebooked on the next one the way any other airline would happily do. And to top it all off, I was given the runaround with 3 different Porter employees diffusing responsibility. I will be moving to Toronto after the wedding but will still work out of Chicago - which means that I could provide business to Porter Airlines for the next few decades! Because of this poor service, you have lost my business. I would rather fly with another airline where customer service is a priority. Losing years of a customer's weekly business over a $150 fee seems to me to be a rather poor business model and I am sorry that the bureaucratic rules in this case could not be bent."

Cons: "The crew were mostly great except one female flight attendant who was unnecessarily rude on two occasions on the short flight."

Cons: "The fee for my bag was too high!"

Pros: "Not sure if this is Porter Airlines or the airport, but the lounge at Billy Bishop Airport is fantastic. Free water, coffee, and snacks - it is so home-y in there, which is amazing when you are away from home :)"

Cons: "N/A"

Pros: "Departing from Billy Bishop is amazing. Incredibly quick and convenient. Complimentary nacks and drinks in the gate area?!"

Pros: "Porter lounge in Toronto"

Cons: "Nothing!"

Pros: "The service"

Cons: "The flight deleyed"

Pros: "Service. Location of both Toronto Island and Chicago Midway are closer to downtown than the bigger airports in each city."

Cons: "Porter was a nice, small, well-kept secret. Now they have expanded quite a bit and the lounge is always full, to the extent that people are sitting all over the ground. Flights are almost always late to take-off. I guess all good things must come to an end."

Book cheap flights from St. John's to Chicago

Recent round-trip flight deals

4/19Wed

2 stopsPorter Airlines

11h 17mYYT-MDW

4/20Thu

3 stopsPorter Airlines

17h 46mMDW-YYT

$491

4/19Wed

2 stopsPorter Airlines

11h 17mYYT-MDW

4/20Thu

2 stopsPorter Airlines

9h 20mMDW-YYT

$519

4/19Wed

3 stopsPorter Airlines

19h 32mYYT-MDW

4/20Thu

3 stopsPorter Airlines

17h 46mMDW-YYT

$526

4/19Wed

3 stopsPorter Airlines

19h 32mYYT-MDW

4/28Fri

2 stopsPorter Airlines

9h 11mMDW-YYT

$575

4/19Wed

2 stopsPorter Airlines

11h 17mYYT-MDW

4/27Thu

2 stopsPorter Airlines

9h 20mMDW-YYT

$598

4/19Wed

1 stopPorter Airlines

11h 17mYYT-MDW

4/28Fri

1 stopPorter Airlines

17h 02mMDW-YYT

$712

4/19Wed

3 stopsPorter Airlines

19h 32mYYT-MDW

4/30Sun

2 stopsPorter Airlines

8h 00mMDW-YYT

$723

4/18Tue

1 stopPorter Airlines

11h 17mYYT-MDW

4/29Sat

3 stopsPorter Airlines

25h 30mMDW-YYT

$854

4/19Wed

1 stopPorter Airlines

11h 17mYYT-MDW

4/30Sun

1 stopPorter Airlines

18h 25mMDW-YYT

$922

4/19Wed

1 stopPorter Airlines

11h 17mYYT-MDW

4/29Sat

3 stopsPorter Airlines

25h 30mMDW-YYT

$925

4/19Wed

1 stopPorter Airlines

11h 17mYYT-MDW

4/29Sat

2 stopsPorter Airlines

47h 10mMDW-YYT

$943

4/18Tue

1 stopPorter Airlines

11h 17mYYT-MDW

4/29Sat

1 stopPorter Airlines

25h 30mMDW-YYT

$982

4/19Wed

1 stopPorter Airlines

11h 17mYYT-MDW

4/29Sat

1 stopPorter Airlines

25h 30mMDW-YYT

$1,054

St. John's - Chicago Flights

Cabin classes:

Browse origins:

$691

St. John's

Browse destinations:

$691

Chicago

YYT - MDW

Find cheap flights from St. John's to Chicago from $491

When to book flights from St. John's to Midway

FAQs for booking St. John's to Chicago flights

How long does a flight from St. John's to Chicago take?

Do I need a passport to fly between St. John's and Chicago?

What’s the cheapest day of the week to fly from St. John's to Chicago?

Which airports will I be using when flying from St. John's to Chicago?

What’s the earliest departure time from St. John's to Chicago?

What’s the latest departure time from St. John's to Chicago?

Which airlines fly nonstop between St. John's and Chicago?

Which aircraft models fly most regularly from St. John's to Chicago?

How does KAYAK find such low prices on flights from St. John's to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from St. John's to Chicago?

What is the Hacker Fare option on flights from St. John's to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from St. John's to Chicago?

Top airline flying St John's to Chicago

Book cheap flights from St. John's to Chicago

Recent round-trip flight deals

Search by stops

Search by airline

Search by price

St. John's - Chicago Flights

Departure:

Destination:

Return flight deals:

Cabin classes:

Browse origins:

Browse destinations: