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Cheap flights from San Juan to Chicago from $119

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 9/25. 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
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
$178Spirit Airlines
Find Deal
vie., oct. 24 - sáb., oct. 25
Spirit Airlines Logo
11:59 am - 10:48 pmSJU-ORD
11h 49m1 stop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$186Spirit Airlines
Find Deal
jue., oct. 2 - lun., oct. 6
Spirit Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$192Spirit Airlines
Find Deal
vie., oct. 24 - lun., oct. 27
Frontier Logo
9:19 pm - 7:10 amSJU-ORD
10h 51m1 stop
Frontier Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
$197Frontier
Find Deal
dom., oct. 26 - mié., oct. 29
Spirit Airlines Logo
11:59 am - 10:48 pmSJU-ORD
11h 49m1 stop
Spirit Airlines Logo
6:00 am - 2:12 pmORD-SJU
7h 12m1 stop
$206Spirit Airlines
Find Deal
vie., oct. 3 - mié., oct. 8
Frontier Logo
5:51 pm - 11:30 amSJU-ORD
18h 39m2 stops
Frontier Logo
5:40 am - 4:54 pmORD-SJU
9h 14m1 stop
$209Frontier
Find Deal
vie., oct. 31 - dom., nov. 2
United Airlines Logo
3:56 pm - 8:03 pmSJU-ORD
5h 07mnonstop
United Airlines Logo
8:55 am - 2:40 pmORD-SJU
4h 45mnonstop
$218United Airlines
Find Deal
vie., oct. 24 - dom., oct. 26
United Airlines Logo
4:55 pm - 11:15 pmSJU-ORD
7h 20m1 stop
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
$223United Airlines
Find Deal
jue., oct. 23 - jue., oct. 30
Delta Logo
1:06 pm - 9:39 pmSJU-ORD
9h 33m1 stop
Delta Logo
7:00 am - 4:25 pmORD-SJU
8h 25m1 stop
$227Delta
Find Deal
mié., oct. 22 - mié., oct. 29
American Airlines Logo
3:00 pm - 7:20 pmSJU-ORD
5h 20mnonstop
American Airlines Logo
8:28 am - 2:08 pmORD-SJU
4h 40mnonstop
$258American Airlines
Find Deal
vie., oct. 24 - dom., oct. 26

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
Oct 26
SJU9:19 pmSan Juan Luis Munoz Marin Intl
10h 51m
1 stop
ORD7:10 amChicago O'Hare Intl
Oct 29
ORD6:40 amChicago O'Hare Intl
10h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
$197
Find similar
Frontier
Oct 31
SJU5:51 pmSan Juan Luis Munoz Marin Intl
18h 39m
2 stops
ORD11:30 amChicago O'Hare Intl
Nov 2
ORD5:40 amChicago O'Hare Intl
9h 14m
1 stop
SJU4:54 pmSan Juan Luis Munoz Marin Intl
$209
Find similar
Frontier
Oct 22
SJU1:59 amSan Juan Luis Munoz Marin Intl
22h 40m
2 stops
ORD11:39 pmChicago O'Hare Intl
Oct 27
ORD6:40 amChicago O'Hare Intl
7h 44m
1 stop
SJU3:24 pmSan Juan Luis Munoz Marin Intl
$226
Find similar

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
Oct 24
SJU7:43 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:57 pmChicago O'Hare Intl
Oct 25
ORD3:00 pmChicago O'Hare Intl
4h 40m
SJU8:40 pmSan Juan Luis Munoz Marin Intl
$178
Find similar
Spirit Airlines
Oct 2
SJU11:59 amSan Juan Luis Munoz Marin Intl
11h 49m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 6
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
$186
Find similar
Spirit Airlines
Oct 24
SJU7:43 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:57 pmChicago O'Hare Intl
Oct 27
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
$192
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 septiembre 17, 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. 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

sáb. 10/25

3:00 pm-8:40 pm

Nonstop4h 40m

$178

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 10/2

11:59 am-10:48 pm

1 stop11h 49m

Chicago O'Hare Intl

lun. 10/6

9:06 pm-2:51 am

Nonstop4h 45m

$186

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

Chicago O'Hare Intl

lun. 10/27

9:06 pm-2:51 am

Nonstop4h 45m

$192

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

dom. 10/26

9:19 pm-7:10 am

1 stop10h 51m

Chicago O'Hare Intl

mié. 10/29

6:40 am-5:54 pm

1 stop10h 14m

$197

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/3

11:59 am-10:48 pm

1 stop11h 49m

Chicago O'Hare Intl

mié. 10/8

6:00 am-2:12 pm

1 stop7h 12m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/31

5:51 pm-11:30 am

2 stops18h 39m

Chicago O'Hare Intl

dom. 11/2

5:40 am-4:54 pm

1 stop9h 14m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/24

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

dom. 10/26

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

jue. 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 10/22

1:06 pm-9:39 pm

1 stop9h 33m

Chicago O'Hare Intl

mié. 10/29

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 10/24

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

dom. 10/26

8:28 am-2:08 pm

Nonstop4h 40m

$258

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Juan averaging around $289.

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 $364. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $516.

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 $253 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $477. 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 $327 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 $268 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

Fastest flight time

5h 07m

Direct flights

Every day
The fastest flight from San Juan to Chicago O'Hare Intl Airport takes 5h 07m
Direct flights go from San Juan to Chicago O'Hare Intl Airport every day.
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 07m.

  • 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 $136Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
7,961 reviews
Search Delta flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
American AirlinesPriceFrom $333Free 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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Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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