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Cheap flights from San Juan to Chicago from $96

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 5/13. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
$145Spirit Airlines
Thu, Feb 26 - Tue, Mar 3
Spirit Airlines Logo
11:03 am - 6:31 pm
SJU
-
ORD
8h 28m
1 stop
Spirit Airlines Logo
10:55 am - 11:58 pm
ORD
-
SJU
12h 03m
1 stop
$159Spirit Airlines
Thu, Apr 9 - Tue, Apr 14
Spirit Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
Spirit Airlines Logo
12:22 pm - 5:54 pm
ORD
-
SJU
4h 32mnonstop
$163Spirit Airlines
Fri, Mar 6 - Wed, Mar 11
Spirit Airlines Logo
11:32 am - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
10:55 am - 11:58 pm
ORD
-
SJU
12h 03m
1 stop
$164Spirit Airlines
Wed, Mar 11 - Wed, Mar 18
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
8:16 pm - 2:31 pm
ORD
-
SJU
17h 15m
1 stop
$168Spirit Airlines
Wed, Mar 4 - Sun, Mar 8
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
$170Spirit Airlines
Thu, Feb 26 - Tue, Mar 3
Multiple Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
Multiple Airlines Logo
8:30 am - 2:53 am
ORD
-
SJU
16h 23m
1 stop
$172Multiple Airlines
Thu, Feb 26 - Tue, Mar 3
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
12:22 pm - 5:54 pm
ORD
-
SJU
4h 32mnonstop
$173Spirit Airlines
Sat, Mar 7 - Wed, Mar 11
Multiple Airlines Logo
11:52 am - 6:18 pm
SJU
-
ORD
8h 26m
1 stop
Multiple Airlines Logo
8:30 am - 2:53 am
ORD
-
SJU
16h 23m
1 stop
$175Multiple Airlines
Thu, Feb 26 - Tue, Mar 3
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
$177Spirit Airlines
Wed, Feb 25 - Sun, Mar 1

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
Feb 25
SJU3:53 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD10:46 amChicago O'Hare Intl
Mar 1
ORD2:13 pmChicago O'Hare Intl
10h 12m
1 stop
SJU2:25 amSan Juan Luis Munoz Marin Intl
$183
Frontier
Feb 19
SJU2:27 pmSan Juan Luis Munoz Marin Intl
18h 39m
1 stop
ORD7:06 amChicago O'Hare Intl
Feb 23
ORD3:50 pmChicago O'Hare Intl
9h 03m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
$202
Frontier
Feb 19
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 28m
1 stop
ORD10:39 pmChicago O'Hare Intl
Feb 23
ORD3:50 pmChicago O'Hare Intl
6h 53m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
$219

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
Feb 26
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
Mar 3
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
$145
Spirit Airlines
Feb 11
SJU1:22 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD4:37 pmChicago O'Hare Intl
Mar 4
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
$147
Spirit Airlines
Feb 12
SJU12:32 pmSan Juan Luis Munoz Marin Intl
5h 16m
ORD3:48 pmChicago O'Hare Intl
Feb 24
ORD12:17 pmChicago O'Hare Intl
4h 32m
SJU6:49 pmSan Juan Luis Munoz Marin Intl
$155

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 February 8, 2026.
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

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 3/3

12:17 pm-6:49 pm

Nonstop4h 32m

$145

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/9

11:03 am-6:31 pm

1 stop8h 28m

Chicago O'Hare Intl

Tue 4/14

10:55 am-11:58 pm

1 stop12h 03m

$159

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 3/6

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Wed 3/11

12:22 pm-5:54 pm

Nonstop4h 32m

$163

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/11

11:32 am-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Wed 3/18

10:55 am-11:58 pm

1 stop12h 03m

$164

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/4

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 3/8

8:16 pm-2:31 pm

1 stop17h 15m

$168

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Tue 3/3

12:17 pm-6:49 pm

Nonstop4h 32m

$170

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 3/3

8:30 am-2:53 am

1 stop16h 23m

$172

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 3/7

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Wed 3/11

12:22 pm-5:54 pm

Nonstop4h 32m

$173

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 3/3

8:30 am-2:53 am

1 stop16h 23m

$175

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 3/1

12:17 pm-6:49 pm

Nonstop4h 32m

$177

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 January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Juan averaging around $293.

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 $376. 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 $538.

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 $256 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $482. 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 $263 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 13m

Direct flights

Every day
The fastest flight from San Juan to Chicago O'Hare Intl Airport takes 5h 13m
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 13m.

  • 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
DeltaPriceFrom $116Free CancellationRating
7.9
8,172 reviews
Search Delta flights
Spirit AirlinesPriceFrom $120Free CancellationRating
6.3
8,430 reviews
Search Spirit Airlines flights
JetBluePriceFrom $131Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
FrontierPriceFrom $137Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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Lake Geneva
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Oak Brook
Orland Park
Racine
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Aurora
South Holland

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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