Cheap flights from San Juan to Chicago from $76
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 10/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from San Juan to Chicago Midway Airport
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How to get the cheapest flight ticket from San Juan to Chicago Midway 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 Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $252. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan during the month September is also very affordable. Most momondo users find prices during this month for around $270.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from San Juan. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday 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 $580.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Juan in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $610. 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 Midway flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best San Juan - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from San Juan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $386 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Juan for as low as $250 on momondo.
What cabin class options are available on San Juan to Chicago Midway flights?
There are 1 cabin classes available to choose from on San Juan to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from San Juan to Chicago Midway Airport on average per week?
As of June 2025, there are 2 flights per week flying from San Juan to Chicago Midway Airport. The most common day of the week flights depart is Sat, with 50% of flights taking off on this day.
Cheap San Juan to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Juan to Chicago Midway Airport
How far is San Juan to Chicago Midway by plane?
The distance between San Juan and Chicago Midway is about 2052.0 mi. In terms of flight time, this usually takes a little over 6h 59m.
When did momondo last update prices for flights from San Juan to Chicago Midway Airport?
Prices for flights from San Juan to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from San Juan to Chicago Midway Airport?
As of June 2025, there are 2 operators available to choose from for flights from San Juan to Chicago Midway Airport.
How old do you have to be to fly from San Juan to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Juan to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway 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 Midway 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 Midway Airport
Compare and see reviews for airlines that fly from San Juan to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $130 | Free Cancellation | Rating 5.9 3,290 reviews | |||
| PriceFrom $312 | Free Cancellation | Rating 8.0 4,278 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from San Juan to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Juan to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from San Juan to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from San Juan which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from San Juan to Chicago?
momondo helps you find the best flight between San Juan and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Juan and alert you when they change.