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Cheap flights from San Juan to Chicago from $109

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 2/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:31 pm - 10:24 pmSJU-ORD
7h 53m1 stop
Multiple Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$178Multiple Airlines
Find Deal
Fr, Dez 5 - Mo, Dez 8
Multiple Airlines Logo
9:00 am - 12:23 pmSJU-ORD
5h 23mnonstop
Multiple Airlines Logo
6:00 am - 8:08 pmORD-SJU
12h 08m1 stop
$180Multiple Airlines
Find Deal
Do, Dez 4 - So, Dez 7
Multiple Airlines Logo
9:00 am - 12:23 pmSJU-ORD
5h 23mnonstop
Multiple Airlines Logo
3:23 pm - 12:49 amORD-SJU
7h 26m1 stop
$183Multiple Airlines
Find Deal
Do, Dez 4 - Mo, Dez 8
Frontier Logo
8:40 am - 11:35 pmSJU-ORD
16h 55m2 stops
Frontier Logo
5:20 am - 3:06 pmORD-SJU
7h 46m1 stop
$186Frontier
Find Deal
Mo, Jan 26 - So, Feb 1
Frontier Logo
6:05 am - 3:23 pmSJU-ORD
11h 18m1 stop
Frontier Logo
8:36 am - 6:23 pmORD-SJU
7h 47m1 stop
$196Frontier
Find Deal
Do, Nov 20 - Mi, Dez 3
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
Frontier Logo
8:00 am - 11:19 amORD-SJU
25h 19m1 stop
$200Frontier
Find Deal
Mi, Nov 12 - Sa, Nov 15
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$217Spirit Airlines
Find Deal
Do, Dez 4 - Mo, Dez 8
Spirit Airlines Logo
6:00 am - 8:09 pmSJU-ORD
16h 09m1 stop
Spirit Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$219Spirit Airlines
Find Deal
Do, Dez 4 - Mo, Dez 8
Spirit Airlines Logo
3:41 pm - 6:51 pmSJU-ORD
5h 10mnonstop
Spirit Airlines Logo
5:10 am - 5:19 pmORD-SJU
10h 09m1 stop
$225Spirit Airlines
Find Deal
Mo, Nov 10 - So, Nov 16
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$231Spirit Airlines
Find Deal
Do, Dez 4 - So, Dez 7

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
Jan 26
SJU8:40 amSan Juan Luis Munoz Marin Intl
16h 55m
2 stops
ORD11:35 pmChicago O'Hare Intl
Feb 1
ORD5:20 amChicago O'Hare Intl
7h 46m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
$186
Find similar
Frontier
Nov 20
SJU6:05 amSan Juan Luis Munoz Marin Intl
11h 18m
1 stop
ORD3:23 pmChicago O'Hare Intl
Dec 3
ORD8:36 amChicago O'Hare Intl
7h 47m
1 stop
SJU6:23 pmSan Juan Luis Munoz Marin Intl
$196
Find similar
Frontier
Nov 12
SJU9:00 amSan Juan Luis Munoz Marin Intl
29h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Nov 15
ORD8:00 amChicago O'Hare Intl
25h 19m
1 stop
SJU11:19 amSan Juan Luis Munoz Marin Intl
$200
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
Nov 13
SJU3:37 pmSan Juan Luis Munoz Marin Intl
10h 50m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 17
ORD8:00 amChicago O'Hare Intl
4h 36m
SJU2:36 pmSan Juan Luis Munoz Marin Intl
$216
Find similar
Spirit Airlines
Dec 4
SJU8:45 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:59 pmChicago O'Hare Intl
Dec 8
ORD5:40 amChicago O'Hare Intl
4h 41m
SJU12:21 pmSan Juan Luis Munoz Marin Intl
$217
Find similar
Spirit Airlines
Dec 4
SJU6:00 amSan Juan Luis Munoz Marin Intl
16h 09m
1 stop
ORD8:09 pmChicago O'Hare Intl
Dec 8
ORD5:40 amChicago O'Hare Intl
4h 41m
SJU12:21 pmSan Juan Luis Munoz Marin Intl
$219
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 November 3, 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

Fr 12/5

4:31 pm-10:24 pm

1 stop7h 53m

Chicago O'Hare Intl

Mo 12/8

5:40 am-12:21 pm

Nonstop4h 41m

$178

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 12/4

9:00 am-12:23 pm

Nonstop5h 23m

Chicago O'Hare Intl

So 12/7

6:00 am-8:08 pm

1 stop12h 08m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 12/4

9:00 am-12:23 pm

Nonstop5h 23m

Chicago O'Hare Intl

Mo 12/8

3:23 pm-12:49 am

1 stop7h 26m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mo 1/26

8:40 am-11:35 pm

2 stops16h 55m

Chicago O'Hare Intl

So 2/1

5:20 am-3:06 pm

1 stop7h 46m

$186

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 11/20

6:05 am-3:23 pm

1 stop11h 18m

Chicago O'Hare Intl

Mi 12/3

8:36 am-6:23 pm

1 stop7h 47m

$196

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mi 11/12

9:00 am-12:45 pm

1 stop29h 45m

Chicago O'Hare Intl

Sa 11/15

8:00 am-11:19 am

1 stop25h 19m

$200

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 12/4

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Mo 12/8

5:40 am-12:21 pm

Nonstop4h 41m

$217

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 12/4

6:00 am-8:09 pm

1 stop16h 09m

Chicago O'Hare Intl

Mo 12/8

5:40 am-12:21 pm

Nonstop4h 41m

$219

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mo 11/10

3:41 pm-6:51 pm

Nonstop5h 10m

Chicago O'Hare Intl

So 11/16

5:10 am-5:19 pm

1 stop10h 09m

$225

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 12/4

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

So 12/7

5:40 am-12:21 pm

Nonstop4h 41m

$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 typical price of a round-trip flight between San Juan and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Juan averaging around $291.

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 $381. 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 $519.

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 $474. 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 $333 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 $271 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 10m

Direct flights

Every day
The fastest flight from San Juan to Chicago O'Hare Intl Airport takes 5h 10m
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 10m.

  • 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
8,114 reviews
Search Spirit Airlines flights
FrontierPriceFrom $139Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
8,001 reviews
Search Delta flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $334Free CancellationRating
7.2
11,036 reviews
Search American Airlines flights
SouthwestPriceFrom $384Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

Traveling to a place near Chicago?

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Lake Geneva
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Orland Park
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Elgin
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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