Cheap flights from Chicago to San Juan

Round-trip
1 adult
Economy
From?
To?
Sun 6/27
Sun 7/4

Flight information for Chicago to San Juan

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan
Best Price Found$136The best flight deal from Chicago to San Juan found on momondo in the last 72 hours is $136
Fastest flight time4h 52mThe fastest flight from Chicago to San Juan takes 4h 52m
Direct flightsSunDirect flights go from Chicago to San Juan on Sunday. Airlines offering direct flights are: American Airlines and Qatar Airways.
Airports in San Juan2 airportsThere are 2 airports near San Juan: San Juan Isla Grande (SIG), San Juan Luis Munoz Marin Intl (SJU)

How to get the cheapest flight ticket from Chicago to San Juan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Chicago to San Juan?

August

The cheapest time of year to fly to San Juan from Chicago is August. Most expensive is December

What is the cheapest day to depart Chicago for San Juan?

Tuesday

The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to San Juan?

at noon

Chicago to San Juan flights are approximately 43% more expensive in the evening than at noon

What is the cheapest airline that flies to San Juan from Chicago?

Spirit Airlines

American Airlines, Delta, and Frontier are the most popular carriers operating from Chicago to San Juan

What is the cheapest Chicago to San Juan flight route?

Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

How far in advance should you book Chicago to San Juan flights?

17 days before

The cheapest time to buy a flight from Chicago to San Juan is approximately 17 days to departure


Easily compare round-trip flights from Chicago to San Juan

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to San Juan by changing tabs
Major Airline
ORDChicago O'Hare Intl
4h 36m
SJUSan Juan Luis Munoz Marin Intl
American Airlines
MDWChicago Midway
6h 11m
SJUSan Juan Luis Munoz Marin Intl

Find the cheapest one-way flights from Chicago to San Juan

If you're looking for one-way flights from Chicago to San Juan, view some of our deals below provided by American Airlines and Major Airline
Major Airline
ORDChicago O'Hare Intl
4h 36m
SJUSan Juan Luis Munoz Marin Intl
American Airlines
MDWChicago Midway
6h 11m
SJUSan Juan Luis Munoz Marin Intl

Best airlines flying from Chicago to San Juan

Compare and see reviews for airlines that fly from Chicago to San Juan with momondo
AirlineRatingFree CancellationPrice
Frontier
PriceFrom $90
Free Cancellation
Rating
7.2
7.6

Boarding

6.8

Comfort

7.8

Crew

6.6

Entertainment

6.8

Food

Reviews

Cons: I asked for a bottle of water because i needed to take my meds and I was given the run around and after i payed i Was given the bottle of water followed by we are about to land in half an hour are you sure?? Of course im sure i need to take my meds. I am a veteran and have to take my meds on time.

1 / 10
Spirit Airlines
PriceFrom $112
Free Cancellation
Rating
7.0
7.4

Boarding

6.7

Comfort

7.6

Crew

6.3

Entertainment

6.4

Food

Reviews

Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.

Cons: Mostly everything.

1 / 10
JetBlue
PriceFrom $151
Free Cancellation
Rating
7.9
8.2

Boarding

8.1

Comfort

8.4

Crew

7.8

Entertainment

7.5

Food

Reviews

Pros: Wayne at the DCA Airport was gracious and amazing.

Cons: The planes still aren’t clean. Pretty sure something was growing on the seat in front of me.

1 / 10
Delta
PriceFrom $163
Free Cancellation
Rating
8.1
8.3

Boarding

8.4

Comfort

8.3

Crew

7.9

Entertainment

8.1

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
United Airlines
PriceFrom $183
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Pros: Everything! From ticketing agent to all the crew on our flight back were awesome. Thank you!

1 / 10
American Airlines
PriceFrom $185
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.9

Crew

7.0

Entertainment

6.8

Food

Reviews

Pros: Delayed flight no reasons seems like American Airlines don’t know what to do in these situations

Cons: I believe this airlines should have figured the answer to this question by now.

1 / 10

  • Which airlines flying from Chicago to San Juan have COVID-19 safety policies in place?

    Airlines such as Alaska Airlines have taken additional precautions to make sure you’re safer while traveling. Usage of HEPA filters, scheduled sanitation, enhanced cleaning of aircrafts, pre-flight testing, and mask policies are some of the implemented practices made by airlines to help keep you safe as you depart from Chicago to San Juan. Keep in mind that policies will vary by airline.

  • Are airlines flying from Chicago to San Juan offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Chicago to San Juan are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, American Airlines, and Spirit Airlines. You can search for the full list of airlines like United Airlines that are offering this flexibility.


Alternative routes for Chicago to San Juan

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
St. Louis to San Juan Flights
Fastest flight time5h 49m
Cheapest price$209


Flights to other cities in Puerto Rico

Lost the lust for San Juan? Check out some flights to other cities in Puerto Rico