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Cheap flights from San Juan to Chicago from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Juan to Chicago departing on 10/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
6:56 am - 3:10 pmORD-SJU
7h 14m1 stop
$179Spirit Airlines
Find Deal
vie., ago. 15 - lun., ago. 18
Spirit Airlines Logo
12:06 pm - 5:55 pmSJU-ORD
6h 49m1 stop
Spirit Airlines Logo
12:55 pm - 6:34 pmORD-SJU
4h 39mnonstop
$186Spirit Airlines
Find Deal
jue., oct. 16 - sáb., oct. 18
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
12:55 pm - 6:40 pmORD-SJU
4h 45mnonstop
$189Spirit Airlines
Find Deal
vie., ago. 15 - lun., ago. 18
Spirit Airlines Logo
7:40 pm - 11:43 pmSJU-ORD
5h 03mnonstop
Spirit Airlines Logo
12:55 pm - 6:40 pmORD-SJU
4h 45mnonstop
$190Spirit Airlines
Find Deal
jue., ago. 14 - lun., ago. 18
Spirit Airlines Logo
7:40 pm - 11:43 pmSJU-ORD
5h 03mnonstop
Spirit Airlines Logo
6:10 am - 11:51 amORD-SJU
4h 41mnonstop
$191Spirit Airlines
Find Deal
jue., ago. 14 - mar., ago. 19
Spirit Airlines Logo
8:00 pm - 9:22 amSJU-ORD
14h 22m1 stop
Spirit Airlines Logo
6:56 am - 3:10 pmORD-SJU
7h 14m1 stop
$192Spirit Airlines
Find Deal
jue., ago. 14 - dom., ago. 17
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
6:56 am - 11:57 pmORD-SJU
16h 01m1 stop
$195Spirit Airlines
Find Deal
vie., ago. 15 - lun., ago. 18
Spirit Airlines Logo
8:00 pm - 9:22 amSJU-ORD
14h 22m1 stop
Spirit Airlines Logo
6:56 am - 11:57 pmORD-SJU
16h 01m1 stop
$200Spirit Airlines
Find Deal
jue., ago. 14 - mar., ago. 19
Logo
4:54 pm - 4:38 pmSJU-ORD
24h 44m1 stop
Logo
6:56 am - 11:57 pmORD-SJU
16h 01m1 stop
$226
Find Deal
sáb., ago. 16 - lun., ago. 18
Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Logo
6:35 am - 11:54 pmORD-SJU
16h 19m1 stop
$231
Find Deal
vie., ago. 15 - jue., ago. 21

Spirit Airlines flights from San Juan to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on San Juan to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
Aug 18
ORD6:56 amChicago O'Hare Intl
7h 14m
1 stop
SJU3:10 pmSan Juan Luis Munoz Marin Intl
$179
Find similar
Spirit Airlines
Oct 16
SJU12:06 pmSan Juan Luis Munoz Marin Intl
6h 49m
1 stop
ORD5:55 pmChicago O'Hare Intl
Oct 18
ORD12:55 pmChicago O'Hare Intl
4h 39m
SJU6:34 pmSan Juan Luis Munoz Marin Intl
$186
Find similar
Spirit Airlines
Aug 15
SJU10:16 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
ORD9:22 amChicago O'Hare Intl
Aug 18
ORD12:55 pmChicago O'Hare Intl
4h 45m
SJU6:40 pmSan Juan Luis Munoz Marin Intl
$189
Find similar

Frontier flights from San Juan to Chicago O'Hare Intl Airport

Our best Frontier deals on San Juan to Chicago O'Hare Intl Airport flight tickets
Frontier
Aug 12
SJU3:40 amSan Juan Luis Munoz Marin Intl
7h 34m
1 stop
ORD10:14 amChicago O'Hare Intl
Sep 13
ORD8:00 amChicago O'Hare Intl
14h 59m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$248
Find similar
Frontier
Aug 8
SJU5:43 pmSan Juan Luis Munoz Marin Intl
7h 42m
1 stop
ORD12:25 amChicago O'Hare Intl
Aug 16
ORD12:20 pmChicago O'Hare Intl
11h 07m
1 stop
SJU12:27 amSan Juan Luis Munoz Marin Intl
$258
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Juan to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated julio 31, 2025.
Use the filters below to find and compare flights from San Juan to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

lun. 8/18

6:56 am-3:10 pm

1 stop7h 14m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 10/16

12:06 pm-5:55 pm

1 stop6h 49m

Chicago O'Hare Intl

sáb. 10/18

12:55 pm-6:34 pm

Nonstop4h 39m

$186

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

lun. 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$189

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

Chicago O'Hare Intl

lun. 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$190

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

7:40 pm-11:43 pm

Nonstop5h 03m

Chicago O'Hare Intl

mar. 8/19

6:10 am-11:51 am

Nonstop4h 41m

$191

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

8:00 pm-9:22 am

1 stop14h 22m

Chicago O'Hare Intl

dom. 8/17

6:56 am-3:10 pm

1 stop7h 14m

$192

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

lun. 8/18

6:56 am-11:57 pm

1 stop16h 01m

$195

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

8:00 pm-9:22 am

1 stop14h 22m

Chicago O'Hare Intl

mar. 8/19

6:56 am-11:57 pm

1 stop16h 01m

$200

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

sáb. 8/16

4:54 pm-4:38 pm

1 stop24h 44m

Chicago O'Hare Intl

lun. 8/18

6:56 am-11:57 pm

1 stop16h 01m

$226

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

jue. 8/21

6:35 am-11:54 pm

1 stop16h 19m

$231

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Juan to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Juan averaging around $257.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $343. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from San Juan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $479.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from San Juan in the evening is the least expensive time of day to depart. momondo users have found prices as low as $243 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Juan to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Juan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Juan for as low as $254 on momondo.

What cabin class options are available on San Juan to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on San Juan to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap San Juan to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Juan to Chicago O'Hare Intl Airport

Best Price Found

$90

Fastest flight time

5h 03m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from San Juan in the past 72 hours is $90. The best round-trip flight deal from San Juan to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $179.
The fastest flight from San Juan to Chicago O'Hare Intl Airport takes 5h 03m
Direct flights go from San Juan to Chicago O'Hare Intl Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, American Airlines and Spirit Airlines.
Search flight deals

  • How far is San Juan to Chicago O'Hare Intl by plane?

    San Juan and Chicago O'Hare Intl are 2067.2 mi apart from one another. A reasonable flight in good conditions will take 5h 03m.

  • When did momondo last update prices for flights from San Juan to Chicago O'Hare Intl Airport?

    Prices for flights from San Juan to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from San Juan to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from San Juan to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San Juan to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from San Juan to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San Juan to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $137Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $329Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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Lake Geneva
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Why use momondo?

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

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

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

Yes. momondo enables you to select and highlight flights to Chicago from San Juan with this policy.

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

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 Chicago from San Juan.

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

If you are not ready to book a flight from San Juan to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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