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Cheap flights from San José to Illinois from $213

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 José to Illinois departing on 10/7. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from San José to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$378Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
9:00 am - 8:30 pm
SJO
-
MDW
10h 30m
1 stop
Southwest Logo
6:05 am - 12:05 pm
MDW
-
SJO
7h 00m
1 stop
$383Southwest
Wed, Oct 7 - Wed, Oct 14
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$403JetBlue
Fri, Aug 28 - Wed, Sep 2
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
$405Southwest
Wed, Sep 23 - Mon, Sep 28
JetBlue Logo
2:02 pm - 11:44 pm
SJO
-
ORD
8h 42m
1 stop
JetBlue Logo
7:00 am - 12:57 pm
ORD
-
SJO
6h 57m
1 stop
$409JetBlue
Thu, Aug 27 - Sun, Aug 30
United Airlines Logo
12:44 pm - 11:44 pm
SJO
-
STL
10h 00m
1 stop
United Airlines Logo
6:14 am - 10:39 pm
STL
-
SJO
17h 25m
1 stop
$569United Airlines
Thu, Jul 23 - Tue, Jul 28
United Airlines Logo
1:25 pm - 8:39 am
SJO
-
STL
18h 14m
2 stops
United Airlines Logo
6:14 am - 7:37 pm
STL
-
SJO
14h 23m
1 stop
$574United Airlines
Thu, Jul 23 - Tue, Jul 28
Delta Logo
2:30 pm - 11:39 pm
SJO
-
STL
9h 09m
1 stop
Delta Logo
6:00 am - 1:05 pm
STL
-
SJO
7h 05m
1 stop
$645Delta
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
6:22 am - 9:08 pm
SJO
-
STL
14h 46m
2 stops
American Airlines Logo
9:38 am - 10:59 pm
STL
-
SJO
13h 21m
1 stop
$654American Airlines
Wed, Nov 25 - Mon, Nov 30
American Airlines Logo
6:22 am - 9:08 pm
SJO
-
STL
14h 46m
2 stops
American Airlines Logo
9:38 am - 10:59 pm
STL
-
SJO
13h 21m
1 stop
$656American Airlines
Wed, Nov 25 - Mon, Nov 30

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JetBlue flights from San José to Illinois

Our best JetBlue deals on San José to Illinois flight tickets
JetBlue
Aug 28
SJO2:02 pmSan José Juan Santamaria Intl
8h 42m
1 stop
ORD11:44 pmChicago O'Hare Intl
Sep 2
ORD7:00 amChicago O'Hare Intl
6h 57m
1 stop
SJO12:57 pmSan José Juan Santamaria Intl
$403
JetBlue
Aug 27
SJO2:02 pmSan José Juan Santamaria Intl
8h 42m
1 stop
ORD11:44 pmChicago O'Hare Intl
Aug 30
ORD7:00 amChicago O'Hare Intl
6h 57m
1 stop
SJO12:57 pmSan José Juan Santamaria Intl
$409
JetBlue
Aug 28
SJO2:02 pmSan José Juan Santamaria Intl
8h 42m
1 stop
ORD11:44 pmChicago O'Hare Intl
Aug 30
ORD7:00 amChicago O'Hare Intl
6h 57m
1 stop
SJO12:57 pmSan José Juan Santamaria Intl
$410

United Airlines flights from San José to Illinois

Our best United Airlines deals on San José to Illinois flight tickets
United Airlines
Dec 22
SJO2:05 pmSan José Juan Santamaria Intl
5h 30m
ORD7:35 pmChicago O'Hare Intl
Jan 5
ORD7:45 amChicago O'Hare Intl
12h 54m
1 stop
SJO8:39 pmSan José Juan Santamaria Intl
$491
United Airlines
Dec 22
SJO2:05 pmSan José Juan Santamaria Intl
5h 30m
ORD7:35 pmChicago O'Hare Intl
Jan 3
ORD9:25 amChicago O'Hare Intl
11h 14m
1 stop
SJO8:39 pmSan José Juan Santamaria Intl
$496
United Airlines
Dec 24
SJO11:28 pmSan José Juan Santamaria Intl
20h 24m
1 stop
ORD7:52 pmChicago O'Hare Intl
Dec 31
ORD9:25 amChicago O'Hare Intl
13h 07m
1 stop
SJO10:32 pmSan José Juan Santamaria Intl
$497

momondo Fare Finder

 
Customize your flight search to find flights from San José to Illinois 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 July 1, 2026.
Use the filters below to find and compare flights from San José to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/16

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Tue 9/22

10:10 am-6:40 pm

2 stops9h 30m

$378

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 10/7

9:00 am-8:30 pm

1 stop10h 30m

Chicago Midway

Wed 10/14

6:05 am-12:05 pm

1 stop7h 00m

$383
Quickest round-trip

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 8/28

2:02 pm-11:44 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 9/2

7:00 am-12:57 pm

1 stop6h 57m

$403

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/23

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Mon 9/28

10:05 am-6:40 pm

2 stops9h 35m

$405

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 8/27

2:02 pm-11:44 pm

1 stop8h 42m

Chicago O'Hare Intl

Sun 8/30

7:00 am-12:57 pm

1 stop6h 57m

$409

San JoséSt. Louis

SJO - STL

SJOSTL

San José Juan Santamaria Intl

Thu 7/23

12:44 pm-11:44 pm

1 stop10h 00m

Lambert-St Louis

Tue 7/28

6:14 am-10:39 pm

1 stop17h 25m

$569

San JoséSt. Louis

SJO - STL

SJOSTL

San José Juan Santamaria Intl

Thu 7/23

1:25 pm-8:39 am

2 stops18h 14m

Lambert-St Louis

Tue 7/28

6:14 am-7:37 pm

1 stop14h 23m

$574

San JoséSt. Louis

SJO - STL

SJOSTL

San José Juan Santamaria Intl

Wed 11/25

2:30 pm-11:39 pm

1 stop9h 09m

Lambert-St Louis

Mon 11/30

6:00 am-1:05 pm

1 stop7h 05m

$645

San JoséSt. Louis

SJO - STL

SJOSTL

San José Juan Santamaria Intl

Wed 11/25

6:22 am-9:08 pm

2 stops14h 46m

Lambert-St Louis

Mon 11/30

9:38 am-10:59 pm

1 stop13h 21m

$654

San JoséSt. Louis

SJO - STL

SJOSTL

San José Juan Santamaria Intl

Wed 11/25

6:22 am-9:08 pm

2 stops14h 46m

Lambert-St Louis

Mon 11/30

9:38 am-10:59 pm

1 stop13h 21m

$656

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 Illinois from

How to get the cheapest flight ticket from San José to Illinois

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 Illinois?

The cheapest month to fly to Illinois from San José is in April. Flight prices, which tend to average around $103, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of April, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $111.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from San José to Illinois is on a Tuesday when prices can be found for as low as $421. Flights from San José to Illinois on a Monday will generally be more expensive and average around $521. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from San José to Illinois during this time can be as low as $464. Flights in the morning are often more expensive with an average ticket price of $467.

What is the cheapest San José Juan Santamaria Intl to Illinois flight route?

Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best San José Juan Santamaria Intl - Illinois flight prices

How far in advance should I book a flight from San José to Illinois?

You are more likely to see cheaper flights to Illinois from San José when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $489 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from San José for as low as $385 on momondo.

What cabin class options are available on San José to Illinois flights?

There are 2 cabin classes available to choose from on San José to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San José to Illinois flights?

You could potentially save up to 4% on your flight if you consider stops on a San José to Illinois flight.

Cheap San José to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Illinois

Best Price Found

$340

Fastest flight time

5h 30m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Illinois

98 airports
The best one-way flight to Illinois from San José in the past 72 hours is $340. The best round-trip flight deal from San José to Illinois found on momondo in the last 72 hours is $701.
The fastest flight from San José to Illinois takes 5h 30m
Direct flights go from San José to Illinois on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 98 airports in Illinois. From San José there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from San José to Illinois

  • When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Illinois?

    Prices for flights from San José Juan Santamaria Intl Airport to Illinois were last updated today.

  • How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Illinois?

  • How old do you have to be to fly from San José Juan Santamaria Intl Airport to Illinois?

    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 José Juan Santamaria Intl Airport to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San José to Illinois?

Best airlines flying from San José to Illinois

Compare and see reviews for airlines that fly from San José to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $189Free CancellationRating
7.6
1,564 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $332Free CancellationRating
7.1
11,765 reviews
Search American Airlines flights
United AirlinesPriceFrom $343Free CancellationRating
7.4
9,909 reviews
Search United Airlines flights
AviancaPriceFrom $375Free CancellationRating
6.5
2,515 reviews
Search Avianca flights
SouthwestPriceFrom $390Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from San José to Illinois?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Illinois from San José.

Can I find flights from San José to Illinois with flexible booking policies on momondo?

Flights from San José to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from San José to Illinois?

Once you have performed a search for San José to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from San José to Illinois right now. Can momondo alert me if prices change?

Price alerts on flights to Illinois from San José are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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