Find Cheap Flights from Chicago to Havana (CHI - HAV)

Flights overview

Useful information for finding cheap flights from Chicago to Havana and booking your next trip

Cheapest round-trip flights	$486	Delta 2 stops 20 hr Sun, Jul 26 — Tue, Aug 4	The cheapest round-trip flight from Chicago to Havana is currently $486
Cheapest one-way flight	$233	Southwest 1 stop 5 hr Tue, Jul 28	The cheapest one-way flight from Chicago to Havana is currently $233
Last-minute weekend getaway	$677	Delta 2 stops 21 hr Sat, May 9 — Mon, May 11	The cheapest last-minute weekend getaway from Chicago to Havana is currently $677
Cheapest business class flights	$1,021	American 1 stop 13 hr Sat, Jul 11 — Fri, Jul 17	The cheapest business class round-trip flight from Chicago to Havana is currently $1,021

Fastest flight	4 hr 50 min	The fastest flight with stops from Chicago to Havana takes 4 hr 50 min
Nonstop flights	None	There are no direct flights on this route.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Havana is typically August. The most expensive month to fly is typically December.

August Cheapest	Typical prices: $425–560
December Most expensive	Typical prices: $500–1,350

Popular airlines from Chicago to Havana

American

from $561

Typical price: $495–660

1034 weekly connecting flights

ORD - HAV Every day
Southwest

from $481

Typical price: $485–720

767 weekly connecting flights

MDW, ORD - HAV Every day
Delta

from $486

Typical price: $490–950

111 weekly connecting flights

MDW, ORD - HAV Every day

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Havana

José Martí international Airport (HAV) (HAV)

Havana Cuba 32 min 10 mi
Juan Gualberto Gómez International Airport (VRA)

Varadero Cuba 1 hr 55 min 59 mi
International Airport "Abel Santamaría Cuadrado" of Santa Clara (SNU)

Santa Clara Cuba 3 hr 42 min 160 mi

Frequently asked questions about flying from Chicago to Havana

The cheapest flights from Chicago to Havana are usually in August. Typical ticket prices in August range from $425 to $560.

The cheapest round-trip flight from Chicago to Havana recently found on Google Flights was with Delta from $486. The cheapest one-way flight was with Southwest from $233.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest American flight from Chicago to Havana is $561, flying from Jul 4 to Jul 10.
The cheapest Southwest flight from Chicago to Havana is $481, flying from Jul 6 to Jul 14.
The cheapest Delta flight from Chicago to Havana is $486, flying from Jul 20 to Jul 28.

The cheapest round-trip flight from Chicago to Havana starts at $486 from Sun, Jul 26 to Tue, Aug 4. The cheapest one-way flight starts at $233 and departs on Tue, Jul 28.

4 hr 50 min is the shortest flight time from Chicago to Havana.

Peak travel season is Dec–May. Hurricanes are possible Jun–Nov. Carnival (Aug) has colorful street parades and a party atmosphere. The International Havana Ballet Festival (Oct, alternate years) is a renowned event running since 1960. The Havana International Jazz Festival (Dec) features large concerts as well as bands playing in cozy bars.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Havana.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Havana really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Havana.

In terms of flights, American is the most popular. American offers 1,034 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to José Martí international Airport (HAV) (HAV) .

Other popular airlines flying from Chicago to Havana are:

Southwest offers 767 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to José Martí international Airport (HAV) (HAV) .
Delta offers 111 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to José Martí international Airport (HAV) (HAV) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Havana.

The cheapest round-trip flight from Chicago to Havana recently found on Google Flights was with Delta from $486. The cheapest one-way flight was with Southwest from $233.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest American flight from Chicago to Havana is $561, flying from Jul 4 to Jul 10.
The cheapest Southwest flight from Chicago to Havana is $481, flying from Jul 6 to Jul 14.
The cheapest Delta flight from Chicago to Havana is $486, flying from Jul 20 to Jul 28.

No airline flies direct from Chicago to Havana.

There are 1034 American connecting flights from Chicago to Havana per week. Flights are available every day.
There are 767 Southwest connecting flights from Chicago to Havana per week. Flights are available every day.
There are 111 Delta connecting flights from Chicago to Havana per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Havana at price $677 is offered by Delta from Sat, May 9 to Mon, May 11.

No airline flies direct from Chicago to Havana.

There are 1034 American connecting flights from Chicago to Havana per week. Flights are available every day.
There are 767 Southwest connecting flights from Chicago to Havana per week. Flights are available every day.
There are 111 Delta connecting flights from Chicago to Havana per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are no direct flights from Chicago to Havana.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Havana, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Havana start at $1,021 from Sat, Jul 11 to Fri, Jul 17 with American.

The cheapest economy class round-trip flights between Chicago and Havana start at $486 from Sun, Jul 26 to Tue, Aug 4.

To book business class trips from Chicago to Havana, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Havana starts at $677 from Sat, May 9 to Mon, May 11 with Delta.

The cheapest last-minute deal between Chicago and Havana at price $677 is offered by Delta from Sat, May 9 to Mon, May 11.

To find last-minute flight deals from Chicago to Havana, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.