SJU - ORD

£100 Find Cheap Flights from San Juan to Chicago – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return flight
£199
Typical prices: £197-£348
United Airlines
Tue 25/12Fri 5/1
SJU - ORD • Direct
Cheapest one-way flight
£100
Typical prices: £117-£241
JetBlue
Sun 9/12
SJU - ORD • 1 stop
Direct flights
You can fly direct with United Airlines, American Airlines, and Frontier. Average duration is 5h 31m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 97% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 26 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 42% price drop
Most popular
Good to know
+1
Good to know
+1
Top stopover airports
Cheapest • Avg £133 (return)
Shortest trip • 7h 33m (one-way)
Insights
Insights
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Juan to Chicago (SJU-ORD)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from San Juan to Chicago

Fri, 25 Dec - Tue, 5 Jan
United Airlines Logo
08:25 - 11:49SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mdirect
United Airlines Logo
14:16 - 21:00ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mdirect
£199United Airlines
Fri, 11 Dec - Mon, 14 Dec
United Airlines Logo
08:25 - 11:49SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mdirect
United Airlines Logo
12:55 - 00:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 41m1 stop Newark
£203United Airlines
Thu, 24 Dec - Thu, 31 Dec
American Airlines Logo
15:01 - 22:50SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 49m1 stop Philadelphia
American Airlines Logo
20:00 - 09:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
11h 36m1 stop Miami
£204American Airlines
Wed, 20 Jan - Mon, 25 Jan
United Airlines Logo
16:55 - 20:26SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mdirect
United Airlines Logo
14:16 - 21:00ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mdirect
£205United Airlines
Thu, 24 Dec - Mon, 4 Jan
United Airlines Logo
07:40 - 16:25SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
10h 45m1 stop Houston George Bush Intcntl
United Airlines Logo
14:25 - 00:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 11m1 stop Newark
£206United Airlines
Fri, 4 Dec - Mon, 7 Dec
United Airlines Logo
16:55 - 20:26SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mdirect
United Airlines Logo
14:16 - 21:00ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mdirect
£207United Airlines
Thu, 24 Dec - Thu, 31 Dec
JetBlue Logo
06:45 - 13:30SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
JetBlue Logo
14:47 - 23:28ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 41m1 stop Fort Lauderdale
£210JetBlue
Tue, 22 Dec - Thu, 31 Dec
JetBlue Logo
06:45 - 13:30SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
JetBlue Logo
14:47 - 23:28ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 41m1 stop Fort Lauderdale
£211JetBlue
Tue, 22 Dec - Thu, 31 Dec
JetBlue Logo
06:45 - 13:30SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 45m1 stop Fort Lauderdale
JetBlue Logo
14:47 - 23:28ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 41m1 stop Fort Lauderdale
£213JetBlue
Wed, 2 Dec - Sun, 6 Dec
United Airlines Logo
16:55 - 20:26SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mdirect
United Airlines Logo
09:21 - 21:24ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
10h 03m1 stop Houston George Bush Intcntl
£213United Airlines
Booking Insights

Price, demand, and travel trends for San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a return flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

Return flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport typically range from £197 to £348. The lowest price found in the past 5 days was £199 on United Airlines.

What's the cheapest day of the week to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. It's 10% cheaper than the average day, while Sunday is the most expensive, with prices 20% higher.

What is the cheapest month to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

•February is the cheapest month to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport at £157 return.
•June (£338) and November (£313) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 115% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport the cheapest?

Flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport are cheapest 26 weeks before departure. Booking in this window typically costs about 22% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights

Low season

October

Cheapest flight

£100
Beat the crowds with an average 27% drop in traveller numbers.
The most popular month to fly with an average 50% increase in traveller numbers.
One-way flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport

When to book flights from San Juan to Chicago

Are your dates flexible? Find out the best times to travel from San Juan to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Your San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • What are the earliest and latest flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    These are the earliest and latest flight times available from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport:

    • Earliest: departs at 05:00 and lands at 10:31
    • Latest: departs at 22:26 and lands at 03:57.

    The flight takes about 5h 31m.

  • How long is a flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    A direct flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport takes 5h 31m, covering 2,073 miles.

  • Do I need a passport to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flight?

    Return flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport range from £197 to £348, with an average of £268 over the past 12 months. Anything below £197 counts as a good deal.

  • How expensive are last-minute San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 2% above the £268 route average. Book 26 weeks before departure for the lowest fares.

  • How much can I save by having a stopover when flying from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    On this route, stopover flights are cheaper than direct options on average. Stopover fares average £133 return via Tampa (TPA), compared with £282 for direct.

  • What is the standard checked bag allowance on flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge £30–£75 for the first checked bag in Economy. Premium fares and elite status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    The Airbus A321neo family is used most often on this route, operated mainly by United Airlines and Frontier. Other aircraft seen on the route include Airbus A320-100/200 variants.

  • How are flight departures from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport spread across the day?

    Morning is the busiest departure period on San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights, with 50% leaving in that window. Afternoon departures account for 50%, Evening flights for 0%, and Night flights for 0%.

  • Which airlines offer Wi-Fi on San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights?

    American Airlines is the only airline on the San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport looking right now?

    One-way fares from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about £118, which is 29% below the typical average for this route.

  • Which car hire options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car hire companies, with daily rates averaging £47 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

  • Which airports can I use when flying from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    Flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport usually depart from San Juan Luis Munoz Marin Intl (SJU) and arrive at Chicago O'Hare Intl (ORD).

  • What time of day has the fewest delays on flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    Morning flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed on the route from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport route, 9% of flights were delayed in the past three months, with delays averaging 3h 20m.

  • Which airports do connecting flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport pass through?

    One-stop flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport most commonly connect through:

    • New York John F Kennedy Intl (JFK) – 34% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) – 23% of one-stop connections
    • Fort Lauderdale (FLL) – 14% of one-stop connections
    • Charlotte Douglas (CLT) – 8% of one-stop connections

  • Can I save money by using flexible dates for flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    Yes. Flexible dates can save you up to 25% on flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. Thursday is the cheapest departure day at £242 return on average, while Sunday is the most expensive at £323, a difference of £81.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • Which airlines fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    3 airlines operate flights between San Juan Luis Munoz Marin Intl Airport and Chicago O'Hare Intl Airport. The airlines offering direct flights on this route include:

    • United Airlines
    • American Airlines
    • Frontier

  • How much time can I save by choosing a different stopover airport from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

    Flying via Tampa (TPA) gives the shortest average 1-stop total travel time of 7h 22m, compared to 7h 33m via Atlanta Hartsfield-Jackson (ATL) and 8h 06m via Charlotte Douglas (CLT).

  • What is the time difference between San Juan Luis Munoz Marin Intl Airport and Chicago O'Hare Intl Airport?

    Chicago O'Hare Intl Airport is 2 hours behind San Juan Luis Munoz Marin Intl Airport (Central Time vs Atlantic Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Grant Park, Magnificent Mile, and United Center. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights?

    Among airlines operating San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Frontier: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy class
    • American Airlines: a cabin bag and a checked bag in Economy class
    • Frontier: a cabin bag in Economy class class

    Baggage allowance can vary by ticket type, cabin class, route, and airline, so always check the fare details before booking.

Your guide to booking San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Sunday. On this route, Thursday flights average £242, about £81 less than Sunday fares (25% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 26 weeks before you fly. On this route, that window historically saves about 22% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport trip for February. Fares historically average £157 return in that month – typically £181 less than the most expensive month, which is June (based on the last 12 months).
  • For the best chance of arriving on time, fly with United Airlines. Over the past three months, 97% of United Airlines flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport arrived on time, slightly above the route average of 91%. When flights on this route arrive late, they're delayed by an average of 3h 20m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through Tampa Airport (TPA) can be cheaper than flying direct. The cheapest stopover option averages £133 return on this route – about £149 less than direct flights (based on the last 12 months).

Prefer to fly direct from San Juan to Chicago?

 
Find which airlines fly direct from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

More options for your flight from San Juan to Chicago

Complete your trip to Chicago with a hotel stay or car hire