Cheap flights from San Juan to Chicago Midway Airport from $64
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 Midway Airport departing on 3/11. 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
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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.
Cheap bus & train deals from San Juan to Chicago
Find recent round-trip train or bus tickets from San Juan to Chicago.
All round-trip flight deals from San Juan to Chicago
The cheapest plane tickets from San Juan to Chicago found on KAYAK recently.
Frontier flights from San Juan to Chicago Midway Airport
Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier![Frontier]()
Feb 26![Frontier]()
Mar 1
SJU7:59 pmSan Juan Luis Munoz Marin Intl
24h 21m
1 stop
MDW6:20 pmChicago Midway
MDW10:26 amChicago Midway
13h 36m
1 stop
SJU2:02 amSan Juan Luis Munoz Marin Intl
Frontier![Frontier]()
Jan 31![Frontier]()
Feb 3
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 54m
1 stop
MDW11:54 amChicago Midway
MDW11:33 amChicago Midway
12h 46m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Southwest flights from San Juan to Chicago Midway Airport
Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest![Southwest]()
Feb 14![Southwest]()
Feb 21
SJU3:30 pmSan Juan Luis Munoz Marin Intl
8h 30m
1 stop
MDW10:00 pmChicago Midway
MDW2:30 pmChicago Midway
8h 30m
2 stops
SJU1:00 amSan Juan Luis Munoz Marin Intl
Southwest![Southwest]()
Feb 19![Southwest]()
Feb 24
SJU12:15 pmSan Juan Luis Munoz Marin Intl
8h 35m
2 stops
MDW6:50 pmChicago Midway
MDW1:25 pmChicago Midway
9h 25m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
See travel insights to Chicago from
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
Prices
Airlines
Other information
What is the cheapest month to fly to Chicago Midway Airport?
The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $244. If you are unable to visit Chicago Midway Airport during the month of February, then departing from San Juan during the month December is also very affordable. Most momondo users find prices during this month for around $252.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from San Juan. The lowest ticket price found for a Sunday departure recently was $247. 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, Wednesday 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 $384.
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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $211 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $353. 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 3 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $312 when searching 3 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 $205 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.
What is the cheapest airline that flies from San Juan to Chicago Midway?
Frontier, Delta, and Southwest are the most popular carriers operating from San Juan to Chicago Midway
What airlines fly to Chicago Midway Airport?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from San Juan according to our data. Frontier is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
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 48m.
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 January 2025, there are 3 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 $124 | Free Cancellation | Rating 6.0 3,435 reviews | |||
| PriceFrom $249 | Free Cancellation | Rating 8.0 8,511 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 8.1 4,659 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsMerrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John
Why use momondo?
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.
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