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Cheap Flights from Ottawa to Chicago Midway

Compare Ottawa to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Ottawa to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Ottawa to Chicago Midway Airport? If you want to travel next month, return fares start from R 7,126. Find the lowest prices on one-way and return tickets right here.
Chicago.R 3,395 per passenger.Departing Wed, 15 Apr.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Wed, 15 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 3,395, select.
Chicago.R 3,465 per passenger.Departing Mon, 15 Jun.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Mon, 15 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 3,465, select.
Chicago.R 3,575 per passenger.Departing Sun, 3 May.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Sun, 3 May, arriving in Chicago Midway.Price includes taxes and charges.From R 3,575, select.
Chicago.R 4,117 per passenger.Departing Fri, 31 Jul.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Fri, 31 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 4,117, select.
Chicago.R 4,593 per passenger.Departing Wed, 12 Aug.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Wed, 12 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 4,593, select.
Chicago.R 5,050 per passenger.Departing Sun, 29 Mar.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Sun, 29 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 5,050, select.
Chicago.R 6,846 per passenger.Departing Thu, 1 Oct.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 6,846, select.
Chicago.R 9,555 per passenger.Departing Fri, 13 Nov.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Fri, 13 Nov, arriving in Chicago Midway.Price includes taxes and charges.From R 9,555, select.

Find the cheapest month to fly from Ottawa to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Ottawa to Chicago Midway flights are currently cheapest in April.
Mar
from R 5,050
Apr
from R 3,395
May
from R 3,575
Jun
from R 3,465
Jul
from R 4,117
Aug
from R 4,593
Sep
Find prices
Oct
from R 6,846
Nov
from R 9,555
Dec
Find prices
Jan
Find prices
Feb
Find prices

Ottawa to Chicago Midway: Alternative routes

Compare routes from Ottawa to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from R 3,395
Search flights

Chicago O'Hare International

25km from central Chicago
from R 3,563
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from R 3,457
Search flights

Ottawa to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 3,395
Cheapest month to flyApril

Finding cheap flights from Ottawa to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Ottawa to Chicago Midway is R 6,588. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Ottawa to Chicago Midway. But we found flights with one stop from R 6,588.
As of March 2026, there are no flights flying from Ottawa to Chicago Midway.
The cheapest month to fly from Ottawa to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Ottawa to Chicago Midway Airport on Tuesday, 5 May 2026.
No airlines currently offer direct flights between Ottawa and Chicago Midway Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Chicago Midway is WestJet .

Flying from Ottawa to Chicago Midway International Airport (MDW): What you need to know

  • Chicago is one hour behind Ottawa. Chicago Midway International Airport is located in Chicago, which runs on the UTC-6 timezone.

  • Get to the airport on time so you don't miss your flight from Ottawa to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to skip the mad dash to your gate.

  • Popular months like August or other busy periods mean longer queues and potential delays. Stick to your schedule by getting to the airport even earlier. Plan for at least four hours ahead of international flights and two hours before domestic departures.

Airports in Ottawa

Ottawa Macdonald-Cartier International Airport (YOW)

  • YOW is around 14 kilometres from central Ottawa. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 20 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 35 minutes.

  • Want an easy start to your travels? Stay near Ottawa Macdonald-Cartier International Airport. Whether you're boarding an early flight from Ottawa to Chicago Midway International Airport or just don't want to be rushed, these hotels are the ideal choice:

  • 58% of flights that leave from Ottawa Macdonald-Cartier International Airport arrive at their destination on schedule.

  • You'll find YOW at 50 Airport Road.

About Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport is around 16 kilometres from the centre of Chicago. It takes around 25 minutes or so to drive to the city.

  • It takes around 30 minutes if you're travelling on public transport.

How to find the cheapest flights from Ottawa to Chicago Midway International Airport (MDW)

  • The cheapest price we've found for a one-way ticket from Ottawa to Chicago Midway International Airport is R 3,395. For a return flight on this route, the best price is R 6,588. Depending on the availability when you book, these fares could change.

  • Booking ahead of time is often the key to finding a cheap flight from Ottawa to MDW. Flight prices rise as demand increases, so the closer you get to departure, the more you'll likely pay.

  • If you can be flexible with your trip dates, try using the 'Whole month' search tool. It'll give you the cheapest price across the month when searching for your Ottawa to Chicago Midway International Airport ticket.

  • There's no need to check every day to find out if prices have dropped when you create a Price Alert. We'll notify you as soon as a better deal is available on plane tickets from Ottawa to MDW.

  • Find an affordable flight from Ottawa to Chicago Midway International Airport by using filters. Choose your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Ottawa to Chicago Midway International Airport (MDW)

  • Think about the pace you're looking for when deciding when to fly. July is the quietest month to go to Chicago. March is when most people book flights from Ottawa to Chicago Midway International Airport (MDW), which may be perfect if you enjoy travelling when it's busier.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Ottawa to MDW plane ticket then if that's your idea of comfortable weather.

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from Ottawa to Chicago Midway International Airport around that time if you like travelling in cooler conditions.

More about Chicago

  • Start your Chicago trip right by choosing the perfect place to stay. Once you've booked your flight from Ottawa to Chicago Midway International Airport, browse our range of accommodation options including:

  • There are so many things to see and do in this city, it can be difficult to know where to begin. Millennium Park, Art Institute of Chicago and Willis Tower are top attractions which should feature on any good Chicago itinerary.

Explore more of the United States

  • You've visited Chicago, now it's time to discover other corners of the United States. Travel around 257 kilometres southeast to Indianapolis to tick off its top attractions. From Lucas Oil Stadium to Eiteljorg Museum and The Children's Museum of Indianapolis, there's plenty to keep you on the go.

  • Milwaukee is another favourite destination in the United States and is around 137 kilometres north of Chicago. No journey is complete without visiting Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan the rest of your trip from Ottawa to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.