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Cheap flights from Chicago to San Juan

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Find the cheapest flights from Chicago to San Juan

Cheap return flights

These are some of the best return flight deals from Chicago to San Juan that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San Juan.

Cheap last-minute flights

Planning a quick getaway from Chicago to San Juan? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Juan, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Chicago to San Juan

Find recent round-trip train or bus tickets from Chicago to San Juan.

All round-trip flight deals to San Juan

The cheapest plane tickets to San Juan found on KAYAK recently.
ORD-SJU
4h 35mdirect
SJU-ORD
5h 25mdirect
American Airlines
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ORD-SJU
4h 38mdirect
SJU-ORD
5h 19mdirect
Air Canada
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ORD-SJU
4h 35mdirect
SJU-ORD
5h 25mdirect
Alaska Airlines
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MDW-SJU
4h 35mdirect
SJU-MDW
5h 30mdirect
Southwest
Find Deal
ORD-SJU
4h 38mdirect
SJU-ORD
5h 19mdirect
Air New Zealand
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ORD-SJU
4h 38mdirect
SJU-ORD
5h 19mdirect
United Airlines
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ORD-SJU
4h 39mdirect
SJU-ORD
5h 24mdirect
Spirit Airlines
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ORD-SJU
4h 35mdirect
American Airlines
Find Deal
ORD-SJU
4h 38mdirect
Air Canada
Find Deal
ORD-SJU
4h 35mdirect
Alaska Airlines
Find Deal
MDW-SJU
4h 35mdirect
Southwest
Find Deal
ORD-SJU
4h 38mdirect
Air New Zealand
Find Deal
ORD-SJU
4h 38mdirect
United Airlines
Find Deal
ORD-SJU
4h 39mdirect
Spirit Airlines
Find Deal

See travel insights to San Juan from

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 to San Juan?

In general, August is the cheapest month to fly from Chicago to San Juan. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around R5 249. If you aren’t able to travel to San Juan during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of R5 249.

What is the cheapest Chicago to San Juan flight route?

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 I book a flight to San Juan?

You are more likely to see cheaper flights to San Juan from Chicago when booking 9 days ahead of your departure date. In general, you can expect to find flights to San Juan for around R6 362 when searching 9 days out. Keep in mind that you might be able to find cheaper flights to San Juan at any time. In fact, our users found flights for as low as R83 865 in the past 72 hours.

What cabin class options are available on Chicago to San Juan flights?

There are 1 cabin classes available to choose from on Chicago to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Direct flights

None
There are no direct flights from Chicago to San Juan. There are no popular flight routes from Chicago to San Juan.

  • How far is Chicago to San Juan by plane?

    Chicago and San Juan are 3302,5 km apart from one another.

  • When did momondo last update prices for flights from Chicago to San Juan?

    Prices for flights from Chicago to San Juan are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago to San Juan?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The required travel and health documents for your San Juan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at San Juan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Juan . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

All flight searches from Chicago to San Juan on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San Juan?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to San Juan from Chicago.

I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San Juan flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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