$59 Cheap flight deals from Chicago (CHI) to Cuba (SGF)

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This Weekend's Flight Deals from Chicago to Cuba

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 25 - Sun, May 26
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$187 Roundtrip, found 7 hours ago
$187
Roundtrip
found 7 hours ago
Select Southern Airways Express flight, departing Sat, May 25 from O'Hare Intl. to Lambert-St. Louis Intl., returning Sun, May 26, priced at $187 found 7 hours ago
Sun, May 26 - Tue, Jun 4
ORD
O'Hare Intl.
SGF
Springfield-Branson National
$299 Roundtrip, found 4 days ago
$299
Roundtrip
found 4 days ago
Select United flight, departing Sun, May 26 from O'Hare Intl. to Springfield-Branson National, returning Tue, Jun 4, priced at $299 found 4 days ago
Sun, May 26 - Mon, Jun 17
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$308 Roundtrip, found 3 days ago
$308
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 26 from Midway Intl. to Lambert-St. Louis Intl., returning Mon, Jun 17, priced at $308 found 3 days ago
Sun, May 26 - Mon, May 27
MDW
Midway Intl.
SGF
Springfield-Branson National
$518 Roundtrip, found 4 days ago
$518
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, May 26 from Midway Intl. to Springfield-Branson National, returning Mon, May 27, priced at $518 found 4 days ago

Airfares from $59 One Way, $97 Round Trip from Chicago to Cuba

Prices starting at $97 for return flights and $59 for one-way flights to Cuba were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jul 1 - Fri, Jul 5
ORD
Chicago
STL
St. Louis
$97 Roundtrip, found 12 hours ago
$97
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Mon, Jul 1 from Chicago to St. Louis, returning Fri, Jul 5, priced at $97 found 12 hours ago
Mon, Jul 1 - Fri, Jul 5
ORD
Chicago
STL
St. Louis
$97 Roundtrip, found 12 hours ago
$97
Roundtrip
found 12 hours ago
Select United flight, departing Mon, Jul 1 from Chicago to St. Louis, returning Fri, Jul 5, priced at $97 found 12 hours ago
Tue, Jun 11 - Sat, Jun 15
ORD
Chicago
STL
St. Louis
$156 Roundtrip, found 9 hours ago
$156
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 11 from Chicago to St. Louis, returning Sat, Jun 15, priced at $156 found 9 hours ago
Tue, Jun 25 - Wed, Jun 26
MDW
Chicago
STL
St. Louis
$186 Roundtrip, found 10 hours ago
$186
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Jun 25 from Chicago to St. Louis, returning Wed, Jun 26, priced at $186 found 10 hours ago
Mon, Jul 22 - Fri, Jul 26
ORD
Chicago
STL
St. Louis
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select Southern Airways Express flight, departing Mon, Jul 22 from Chicago to St. Louis, returning Fri, Jul 26, priced at $187 found 2 hours ago

Cuba economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Suites at Fall Creek
3.0-star property

The Suites at Fall Creek

8.4/10 Very Good! (1,001 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Springfield (SGF)

American Airlines • Roundtrip • Coach
per person
The property was quiet and peaceful. We will be returning.

Reviewed on Apr 21, 2024

Westgate Branson Woods Resort and Cabins
3.5-star property

Westgate Branson Woods Resort and Cabins

6.8/10 (1,002 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Springfield (SGF)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
Beautiful property and great for families. We will only stay at this resort again.

Reviewed on Oct 24, 2022

Still Waters Resort
4.0-star property

Still Waters Resort

8.8/10 Excellent! (3,560 reviews)

Jun 16 - Jun 19

3 night stay

Chicago (MDW) to Springfield (SGF)

Delta • Non-stop roundtrip • Coach
per person
We didnt originally plan to stay here, but we drove past the place we had booked and decided to find something nicer. We saw this Stillwater and thought we were dreaming. We booked a night and then a few more. The staff was super accommodating as we messed up our reservations. Our room/condo was fabulous. Clean and welcomimg and comfortable. Sitting on the patio and watching the ducks was so relaxing. 2 of the pools were open. The oasis pool is amazing and the gentleman that was there (sorry i forgot his name!), was friendly and fun. There are water sports and hiking and just all around joy. We came pre-season, so i can only imagine how awesome full season is. We will be back! Also, a special thanks to Trevor and the front desk for all your help to keep us in our room after i messed up the 2nd reservation

Reviewed on May 5, 2024

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More About Flying To Cuba from Chicago

Route Information for Flights from Chicago to Cuba

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SGF
Distance
258 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, Austrian, Aer Lingus, Emirates, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Turkish Airlines, Royal Jordanian, Finnair, Iberia, ANA, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
2:19PM UTC
Latest Flight Arrival
2:47AM UTC

Chicago to Cuba

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.