Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.

Flights
Hotels
Round-trip
One-way
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.
Did you mean flights from Havana to Chicago?

Flights from Chicago to Havana, Cuba Last modified: Sep 30, 2016 1:10 -04:00

Chicago to Havana Last modified: Sep 30, 2016 1:10 -04:00

We've scanned 26,216,477,370 round trip itineraries and found the cheapest flights from Chicago to Havana. AeroMexico & Copa frequently offer the best deals on Chicago to Havana flights, or select your preferred carrier below to see the cheapest days to fly.

AeroMexico
CHIHAV
Wed 10/26
2 stops
HAVCHI
Sat 10/29
2 stops
$249
Select
AeroMexico
CHIHAV
Thu 10/27
2 stops
HAVCHI
Fri 11/4
2 stops
$249
Select
AeroMexico
CHIHAV
Sat 10/29
2 stops
HAVCHI
Fri 11/4
2 stops
$249
Select
AeroMexico
CHIHAV
Sun 10/30
2 stops
HAVCHI
Mon 11/7
2 stops
$249
Select
AeroMexico
CHIHAV
Tue 11/1
2 stops
HAVCHI
Thu 11/10
2 stops
$249
Select
Copa
CHIHAV
Thu 1/19
1 stop
HAVCHI
Wed 1/25
1 stop
$252
Select
American
CHIHAV
Thu 12/8
1 stop
HAVCHI
Tue 12/13
1 stop
$278
Select
American
CHIHAV
Fri 1/13
1 stop
HAVCHI
Mon 1/16
1 stop
$278
Select
American
CHIHAV
Thu 1/26
1 stop
HAVCHI
Mon 1/30
1 stop
$278
Select
American
CHIHAV
Fri 1/27
1 stop
HAVCHI
Thu 2/2
1 stop
$278
Select
United
CHIHAV
Sun 1/1
1 stop
HAVCHI
Sat 1/14
1 stop
$278
Select
Spirit
CHIHAV
Thu 12/1
1 stop
HAVCHI
Thu 12/8
1 stop
$325
Select
Cayman
CHIHAV
Wed 1/25
1 stop
HAVCHI
Tue 1/31
1 stop
$670
Select

How Much is a Flight from Chicago to Havana?

We have collected flight cost data from across the web for travel from Chicago to Havana, and have found the average flight price for this trip to be $249.

Where To Buy Cheap Flights from Chicago to Havana?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Havana based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Chicago to Havana?

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Havana.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $0 $326
7-14 days $0 $393
14-21 days $0 $326
21-30 days $0 $249
30-60 days $0 $249
60-90 days $0 $249
90+ days $0 $249

Cheapest Day To Fly from Chicago to Havana

We've examined 26,224,294,390 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Havana is Sunday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$249 $249 $249 $249 $249 $249 $249

Compare Flight Prices from Chicago to Havana by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to Havana flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
October Chicago Havana AeroMexico 10/26/16 10/29/16 2 $249
November Chicago Havana AeroMexico 11/1/16 11/10/16 2 $249
December Chicago Havana AeroMexico 12/1/16 12/8/16 1 $249
January Chicago Havana AeroMexico 1/14/17 1/21/17 2 $249
February Chicago Havana Copa 2/15/17 2/22/17 1 $252
March Chicago Havana Copa 3/6/17 3/10/17 1 $250
April Chicago Havana American 4/23/17 4/26/17 2 $304
May Chicago Havana AeroMexico 5/4/17 5/7/17 2 $249

Cheap Last Minute Flights from Chicago to Havana

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Havana. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
2 3 4 5 6 7 8
$600
9 10 11 12 13 14 15
$600
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31 1 2 3 4 5
$393
6 7 8 9 10 11 12
$393

Connecting Flights vs Direct Flights from Chicago to Havana

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Havana is $357.

The average price for direct flights from Chicago to Havana is not available.

One Way Flights vs Round Trip Flights from Chicago to Havana

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Havana. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Havana is $123.

The average price for round trip flights from Chicago to Havana is $266.

Chicago to Havana Flight Questions

Below are some common questions that asked about this flight route:

Question: What are the most popular connecting cities when flying from Chicago to Havana?
Answer: Mexico City, MX

Airlines in Chicago flying to Havana Last modified: Sep 30, 2016 1:10 -04:00Number of routes searched: 70Number of itineraries searched: 17,331

Wondering which airlines fly out of Chicago to Havana? We've gathered the average price of Chicago airlines with flights to Havana. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Chicago to Havana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
Interjet MEX
American CLT
American MIA
Air France CDG
AeroMexico GDL
AeroMexico MEX
Copa PTY
Delta ATL
Delta JFK
Cayman GCM
Swiss ZRH
Spirit FLL
Austrian VIE
United EWR
United IAH
American ATL / CLT
American ATL / MIA
American BNA / CLT
AeroMexico GDL / CUN
AeroMexico GDL / MEX
AeroMexico MEX / CUN
Delta ATL / JFK
Delta ATL / MIA
Delta DTW / ATL

Chicago to Havana Airports

These are the major commercial airports we're currently monitoring in Chicago and Havana. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Ft Lauderdale American, JetBlue, Delta, Spirit, United $142
Flights from Chicago to Tampa American, Delta, Frontier, Spirit, United $87
Flights from Chicago to Ft Myers American, Delta, Spirit, United $157
Flights from Chicago to Key West American, Delta, United $323
Flights from Chicago to Houston American, Delta, Spirit, United $81
Flights from Chicago to West Palm Beach American, JetBlue, Delta, Frontier, United $77
Flights from Chicago to New Orleans American, Delta, Spirit $79
Flights from Chicago to Phoenix American, Alaska, Delta, Frontier, Spirit, United $107
Flights from Chicago to Sarasota - Bradenton American, Delta, United $201
Flights from Chicago to Boston American, JetBlue, Delta, Spirit, United $81
Flights from Chicago to Minneapolis - St Paul Delta, Spirit $79
Flights from Chicago to Charlotte American, Alaska, Delta, Frontier, United $85
Flights from Chicago to Newark American, Delta, United $137
Flights from Chicago to Seattle American, Alaska, Delta, Frontier, Spirit, United, Virgin America $127
Flights from Chicago to Detroit American, Delta $168
Flights from Chicago to Nashville American, Delta, Frontier $97
Flights from Chicago to Baltimore American, Delta, Spirit, United $81

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Cancun American, Air Canada, AeroMexico, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet, Volaris $303
Flights from Chicago to Toronto American, Air Canada, Delta, Porter, United, WestJet $214
Flights from Chicago to Montego Bay American, Air Canada, JetBlue, British Airways, Delta, Spirit, United, WestJet $388
Flights from Chicago to Mexico City Interjet, American, Air Canada, AeroMexico, British Airways, Delta, United, WestJet, Volaris $262
Flights from Chicago to Grand Cayman American, Delta, Cayman, United, WestJet $470
Flights from Chicago to Cozumel American, Air Canada, AeroMexico, Delta, United, WestJet $402
Flights from Chicago to London Jet Airways, American, Air Berlin, Air Canada, Air France, Finnair, British Airways, Delta, Aer Lingus, Icelandair, Iberia, KLM, Lufthansa, Austrian, Qatar, SAS, Brussels, United, Virgin Atlantic, WestJet $506
Flights from Chicago to Nassau American, Air Berlin, Air Canada, JetBlue, British Airways, Copa, Delta, United, WestJet $373

Cheap Domestic Flights to Havana - HAV

Cheap Flights from Chicago to Havana