Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from San Juan to Chicago from $101

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 1/12. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
11:15 am - 7:45 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$169JetBlue
Wed, Feb 11 - Wed, Mar 4
JetBlue Logo
5:22 pm - 11:10 pm
SJU
-
ORD
7h 48m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$171JetBlue
Thu, Feb 12 - Fri, Feb 27
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
7:45 am - 6:02 pm
ORD
-
SJU
8h 17m1 stop
$173JetBlue
Wed, Feb 4 - Sun, Feb 8
Frontier Logo
8:00 am - 10:41 am
SJU
-
ORD
28h 41m1 stop
Frontier Logo
6:03 am - 5:00 pm
ORD
-
SJU
8h 57m1 stop
$176Frontier
Wed, Jan 21 - Sat, Jan 24
Frontier Logo
5:25 pm - 3:52 pm
SJU
-
ORD
24h 27m1 stop
Frontier Logo
4:42 pm - 1:57 am
ORD
-
SJU
7h 15m1 stop
$177Frontier
Tue, Feb 10 - Sat, Feb 14
Multiple Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
Multiple Airlines Logo
7:45 am - 6:05 pm
ORD
-
SJU
8h 20m1 stop
$178Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
JetBlue Logo
11:06 am - 7:31 pm
SJU
-
ORD
10h 25m1 stop
JetBlue Logo
7:45 am - 6:02 pm
ORD
-
SJU
8h 17m1 stop
$179JetBlue
Thu, Feb 5 - Sun, Feb 8
JetBlue Logo
1:44 pm - 11:10 pm
SJU
-
ORD
11h 26m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$180JetBlue
Thu, Feb 12 - Fri, Feb 27
Frontier Logo
2:29 am - 2:22 pm
SJU
-
ORD
13h 53m1 stop
Frontier Logo
8:08 pm - 2:30 am
ORD
-
SJU
28h 22m1 stop
$181Frontier
Sun, Jan 11 - Thu, Jan 15
Multiple Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
Multiple Airlines Logo
9:15 am - 7:26 pm
ORD
-
SJU
8h 11m1 stop
$183Multiple Airlines
Wed, Jan 28 - Fri, Jan 30

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

Our best JetBlue deals on San Juan to Chicago O'Hare Intl Airport flight tickets
JetBlue
Feb 11
SJU11:15 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:45 pmChicago O'Hare Intl
Mar 4
ORD12:41 pmChicago O'Hare Intl
9h 03m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
$169
Find similar
JetBlue
Feb 12
SJU5:22 pmSan Juan Luis Munoz Marin Intl
7h 48m
1 stop
ORD11:10 pmChicago O'Hare Intl
Feb 27
ORD12:41 pmChicago O'Hare Intl
9h 03m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
$171
Find similar
JetBlue
Feb 4
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
Feb 8
ORD7:45 amChicago O'Hare Intl
8h 17m
1 stop
SJU6:02 pmSan Juan Luis Munoz Marin Intl
$173
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
Jan 21
SJU8:00 amSan Juan Luis Munoz Marin Intl
28h 41m
1 stop
ORD10:41 amChicago O'Hare Intl
Jan 24
ORD6:03 amChicago O'Hare Intl
8h 57m
1 stop
SJU5:00 pmSan Juan Luis Munoz Marin Intl
$176
Find similar
Frontier
Feb 10
SJU5:25 pmSan Juan Luis Munoz Marin Intl
24h 27m
1 stop
ORD3:52 pmChicago O'Hare Intl
Feb 14
ORD4:42 pmChicago O'Hare Intl
7h 15m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
$177
Find similar
Frontier
Feb 19
SJU4:25 pmSan Juan Luis Munoz Marin Intl
29h 47m
1 stop
ORD8:12 pmChicago O'Hare Intl
Feb 23
ORD5:05 amChicago O'Hare Intl
7h 57m
1 stop
SJU3:02 pmSan Juan Luis Munoz Marin Intl
$181
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 December 18, 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

Wed 2/11

11:15 am-7:45 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 3/4

12:41 pm-11:44 pm

1 stop9h 03m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/12

5:22 pm-11:10 pm

1 stop7h 48m

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

$171

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/4

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$173

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

8:00 am-10:41 am

1 stop28h 41m

Chicago O'Hare Intl

Sat 1/24

6:03 am-5:00 pm

1 stop8h 57m

$176

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 2/10

5:25 pm-3:52 pm

1 stop24h 27m

Chicago O'Hare Intl

Sat 2/14

4:42 pm-1:57 am

1 stop7h 15m

$177

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 1/25

7:45 am-6:05 pm

1 stop8h 20m

$178

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/12

1:44 pm-11:10 pm

1 stop11h 26m

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 1/11

2:29 am-2:22 pm

1 stop13h 53m

Chicago O'Hare Intl

Thu 1/15

8:08 pm-2:30 am

1 stop28h 22m

$181

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/28

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Fri 1/30

9:15 am-7:26 pm

1 stop8h 11m

$183

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $296.

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 $385. 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 $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 $257 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $472. 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 $337 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 $287 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 15m

Direct flights

Every day
The fastest flight from San Juan to Chicago O'Hare Intl Airport takes 5h 15m
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 15m.

  • 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
JetBluePriceFrom $120Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $138Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
FrontierPriceFrom $138Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
8,009 reviews
Search Delta flights
American AirlinesPriceFrom $259Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights
United AirlinesPriceFrom $271Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
SouthwestPriceFrom $341Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
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.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 1/17
Sat 1/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago