Cheap flights from San Juan to Chicago from $69
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 5/29. 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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1 adult
Economy
0 bags
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Cheap round-trip flights
These are some of the best round-trip flight deals from San Juan to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Juan to Chicago.
Cheap last minute flights
Planning a quick getaway from San Juan to Chicago? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.
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![Spirit Airlines]()
May 29![Spirit Airlines]()
Jun 1
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
ORD8:17 amChicago O'Hare Intl
10h 45m
1 stop
SJU8:02 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines![Spirit Airlines]()
May 29![Spirit Airlines]()
Jun 1
SJU8:12 pmSan Juan Luis Munoz Marin Intl
13h 38m
1 stop
ORD8:50 amChicago O'Hare Intl
ORD8:17 amChicago O'Hare Intl
10h 45m
1 stop
SJU8:02 pmSan Juan Luis Munoz Marin Intl
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![Frontier]()
May 7![Frontier]()
May 12
SJU3:56 amSan Juan Luis Munoz Marin Intl
20h 36m
1 stop
ORD11:32 pmChicago O'Hare Intl
ORD4:15 pmChicago O'Hare Intl
9h 36m
1 stop
SJU2:51 amSan Juan Luis Munoz Marin Intl
Frontier![Frontier]()
May 9![Frontier]()
May 24
SJU3:56 amSan Juan Luis Munoz Marin Intl
20h 36m
1 stop
ORD11:32 pmChicago O'Hare Intl
ORD5:03 pmChicago O'Hare Intl
8h 29m
1 stop
SJU2:32 amSan Juan Luis Munoz Marin Intl
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
Prices
Airlines
Other information
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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Juan averaging around $233.
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 $322. 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 $436.
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 $241 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $473. 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 4 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $304 when searching 4 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 $233 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.
What is the cheapest airline that flies from San Juan to Chicago O'Hare Intl?
Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from San Juan to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San Juan according to our data. Spirit Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Juan to Chicago O'Hare Intl Airport on average per day?
6 flights are operational daily from San Juan to Chicago O'Hare Intl Airport as of April 2025. The most popular departure time for this route is 7:00AM, with 56% of flights per day taking off in the afternoon.
How many flights depart from San Juan to Chicago O'Hare Intl Airport on average per week?
46 flights are operational weekly from San Juan to Chicago O'Hare Intl Airport as of April 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.
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
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 4h 58m.
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?
As of April 2025, there are 6 operators available to choose from 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 | ||
|---|---|---|---|---|---|
| PriceFrom $137 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 6.3 7,956 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 8.0 7,929 reviews | |||
| PriceFrom $215 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $257 | Free Cancellation | Rating 8.0 4,295 reviews | |||
| PriceFrom $326 | Free Cancellation | Rating 7.2 10,000 reviews |
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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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