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Fast facts on flights from Chicago

Cheapest flight ticket foundChicago Midway, Chicago O'Hare International
Cheapest route foundC$90
Cheapest month to flyJuly
Most popular airlineAmerican Airlines
Most popular destinationToronto

The best flight deals leaving from Chicago soon

Looking for a cheap last-minute deal or the best return flight from Chicago? If you want to travel from Chicago next month, return fares start from C$90. Find the lowest prices on one-way and return tickets right here.
Nashville.C$91 per passenger.Departing Sun., Jul. 12, returning Thu., Jul. 16.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sun., Jul. 12, arriving in Nashville.Inbound direct flight with Allegiant Air departs from Nashville on Thu., Jul. 16, arriving in Chicago Rockford.Price includes taxes and charges.From C$91, select.
San Juan.C$197 per passenger.Departing Tue., Aug. 18, returning Tue., Sep. 1.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue., Aug. 18, arriving in San Juan Luis Munoz Marin.Inbound direct flight with Frontier Airlines departs from San Juan Luis Munoz Marin on Tue., Sep. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$197, select.
Monterrey.C$237 per passenger.Departing Thu., Jan. 21, returning Fri., Feb. 12.Return flight with Viva.Outbound direct flight with Viva departs from Chicago O'Hare International on Thu., Jan. 21, arriving in Monterrey Gen Mariano Escobedo.Inbound direct flight with Viva departs from Monterrey Gen Mariano Escobedo on Fri., Feb. 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$237, select.
Toronto.C$271 per passenger.Departing Thu., Sep. 3, returning Sun., Sep. 6.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago O'Hare International on Thu., Sep. 3, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun., Sep. 6, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$271, select.
Nassau.C$413 per passenger.Departing Wed., Aug. 19, returning Sat., Aug. 22.Return flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Wed., Aug. 19, arriving in Nassau International.Inbound indirect flight with jetBlue, departs from Nassau International on Sat., Aug. 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$413, select.
Punta Cana.C$434 per passenger.Departing Fri., Oct. 30, returning Sat., Nov. 7.Return flight with Arajet.Outbound direct flight with Arajet departs from Chicago O'Hare International on Fri., Oct. 30, arriving in Punta Cana.Inbound direct flight with Arajet departs from Punta Cana on Sat., Nov. 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$434, select.
San Jose.C$437 per passenger.Departing Fri., Sep. 11, returning Tue., Sep. 15.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri., Sep. 11, arriving in San Jose Juan Santamaria.Inbound indirect flight with Southwest Airlines, departs from San Jose Juan Santamaria on Tue., Sep. 15, arriving in Chicago Midway.Price includes taxes and charges.From C$437, select.
Montego Bay.C$444 per passenger.Departing Wed., Sep. 16, returning Wed., Sep. 23.Return flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Wed., Sep. 16, arriving in Montego Bay.Inbound indirect flight with jetBlue, departs from Montego Bay on Wed., Sep. 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$444, select.
Havana.C$467 per passenger.Departing Sat., Aug. 15, returning Sat., Aug. 29.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat., Aug. 15, arriving in Havana.Inbound indirect flight with Viva, departs from Havana on Sat., Aug. 29, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$467, select.
Cartagena.C$488 per passenger.Departing Sun., Jul. 12, returning Fri., Jul. 17.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Sun., Jul. 12, arriving in Cartagena.Inbound indirect flight with Copa, departs from Cartagena on Fri., Jul. 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$488, select.
Guatemala City.C$510 per passenger.Departing Sun., Sep. 20, returning Wed., Sep. 30.Return flight with Allegiant Air and jetBlue.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun., Sep. 20, arriving in Guatemala City.Inbound indirect flight with jetBlue, departs from Guatemala City on Wed., Sep. 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$510, select.
Dublin.C$522 per passenger.Departing Tue., Sep. 1, returning Thu., Sep. 17.Return flight with Aer Lingus.Outbound indirect flight with Aer Lingus, departs from Chicago O'Hare International on Tue., Sep. 1, arriving in Dublin.Inbound indirect flight with Aer Lingus, departs from Dublin on Thu., Sep. 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$522, select.
Guayaquil.C$528 per passenger.Departing Fri., Sep. 18, returning Mon., Sep. 21.Return flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Fri., Sep. 18, arriving in Guayaquil.Inbound indirect flight with jetBlue, departs from Guayaquil on Mon., Sep. 21, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$528, select.
Philipsburg.C$542 per passenger.Departing Thu., Oct. 1, returning Sun., Oct. 4.Return flight with jetBlue.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Thu., Oct. 1, arriving in St Maarten.Inbound indirect flight with jetBlue, departs from St Maarten on Sun., Oct. 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$542, select.
San Pedro Sula.C$545 per passenger.Departing Mon., Oct. 19, returning Sun., Oct. 25.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Mon., Oct. 19, arriving in San Pedro Sula.Inbound indirect flight with Copa, departs from San Pedro Sula on Sun., Oct. 25, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$545, select.
San Salvador.C$576 per passenger.Departing Thu., Sep. 10, returning Sun., Sep. 13.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Thu., Sep. 10, arriving in San Salvador.Inbound indirect flight with United, departs from San Salvador on Sun., Sep. 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$576, select.
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Booking flights from Chicago: frequently asked questions

The best price we found for a return flight from Chicago to Nashville is C$90. 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.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly out of Chicago is Sunday, July 12, 2026, to Nashville.
It's easy with us. Look for cheap flights and flight offers from Chicago to anywhere using Everywhere search– it'll show you the lowest fares for your chosen time period.

You can also set up Price Alerts for flights you'd like to keep an eye on. We'll let you know when a particular fare from Chicago rises or falls so you can book when it's cheapest.
Sure – our flight search allows you to check for outbound flights from Chicago Rockford Airport departing the very same day. But if you want the cheapest fare, we recommend you book around 30 days before departure. This is on average, the time when fares are cheaper.
Of course! Just select 'one way' when you search with us. And here's an extra tip: sometimes searching for a one way ticket from Chicago, and another one-way back home, can yield cheaper tickets than a return fare with an airline.
It's best to arrive at the airport at least 2 hours before the time of your flight departure, so you have enough time to check any luggage in, clear security and find your gate.
The cheapest flight from Chicago we found in the next 1 year is to Nashville for C$91. It departs from Chicago Rockford Airport on Sunday, July 12, 2026. There are also cheap flights from Chicago to San Juan Luis Munoz Marin for C$197 and Monterrey Gen Mariano Escobedo for C$237.

How to find cheap flights from Chicago

  • The lowest price we've found for a one-way flight from Chicago is C$42, leaving from Chicago Rockford.

  • Fares for a return journey start at C$91.

  • The cheapest city you can fly to from Chicago is Nashville.

  • Comparing flights across different airports in Chicago can help you cut travel costs. Check out the fares from Chicago O'Hare International Airport (ORD), Chicago Midway Airport (MDW) and Chicago Rockford Airport (RFD).

  • Have the best deals come straight to you by creating a Price Alert for the flights you're interested in. You'll get an email or a notification through the app when prices drop.

  • Choose the right time when booking your plane tickets from Chicago. For domestic travel, try to secure your seats one to three months before departure, while international trips are often best locked in two to six months in advance.

  • Potentially find lower prices by selecting 'Add nearby airports' at the start of your search. This widens your results to include nearby airports at your destination.

  • Don't know where you want to go? Enter your departure city (Chicago), then choose 'Explore everywhere' to find flights to any destination ordered by price.

Flying from Chicago: what you need to know

  • All departures from Chicago are listed in the local UTC-6 time zone.

  • Here's an overview of the leading airlines flying from Chicago, with one example of an airport they operate from:

  • Visiting another country? Entry rules can vary depending on your length of stay, passport and travel plans, so always check ahead. Airlines and official embassy sites will have the most up-to-date advice on visas or any other documentation you may need.

Best time to fly from Chicago

  • July is usually when flights departing from Chicago are at their cheapest.

  • July is generally the most popular month to travel. You can expect more flight choices during busy periods like this, but you can also expect to pay more.

  • More affordable tickets are available in December, which is the least busy time to fly out of the city.

  • One travel tip worth knowing: go midweek. Flights from Chicago leaving on Tuesdays and Wednesdays usually cost less than weekend departures.

Where to fly to from Chicago

  • Take your pick from cities including Toronto, London and Montreal. They're among the most popular international destinations to travel to from Chicago.

  • Go-to options for domestic getaways include New York, Washington DC and Atlanta.

  • Want to stretch your travel plans a little further? When flying from Chicago, the most visited countries include Canada, Mexico and the United Kingdom.

  • Coming in at around 45 minutes, the shortest flight out of Chicago will bring you to Milwaukee.

Leaving from Chicago O'Hare International Airport (ORD)

Flying out of Chicago Midway Airport (MDW)

Chicago Rockford Airport (RFD) departures

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