Cheap flights from Chicago Midway Airport to San Juan from $145
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Juan departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to San Juan
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Frontier flights from Chicago Midway Airport to San Juan
Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Delta flights from Chicago Midway Airport to San Juan
Our best Delta deals on Chicago Midway Airport to San Juan flight tickets
See travel insights to San Juan from
How to get the cheapest flight ticket from Chicago Midway Airport to San Juan
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 San Juan?
If you’re not able to fly to San Juan in May, then August is your next best option. Flight prices from Chicago Midway Airport to San Juan during August average around $312.
What is the cheapest day to depart on your flight to San Juan?
The cheapest day to depart from Chicago Midway Airport to San Juan is on a Tuesday when prices can be found for as low as $365. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $421.
What is the cheapest time of day to depart on your flight to San Juan?
The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $298. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $409 on average. Flights to San Juan from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago Midway to San Juan flight route?
Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - San Juan flight prices
How far in advance should I book a flight to San Juan?
You are more likely to see cheaper flights to San Juan from Chicago Midway Airport when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $402 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago Midway Airport for as low as $298 on momondo.
What cabin class options are available on Chicago Midway to San Juan flights?
There are 1 cabin classes available to choose from on Chicago Midway to San Juan 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 Chicago Midway to San Juan?
Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to San Juan
What airlines fly to San Juan?
Southwest, Frontier and Delta are the top three most popular airlines that fly to San Juan from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 45% of people opting to fly with this airline when traveling to San Juan. Keep in mind that there are 4 different airlines that fly to San Juan on a routine basis, so you have a few additional options to choose from.
Cheap Chicago Midway Airport to San Juan flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Juan
How far is Chicago Midway to San Juan by plane?
The straight-line distance from Chicago Midway to San Juan is 2052.0 mi. 4h 40m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago Midway Airport to San Juan?
Prices for flights from Chicago Midway Airport to San Juan are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to San Juan?
As of April 2025, there are 4 operators available to choose from for flights from Chicago Midway Airport to San Juan.
How old do you have to be to fly from Chicago Midway Airport to San Juan?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to San Juan.
What documentation or ID do you need to fly to San Juan?
The necessary travel and health documents for your San Juan 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.
Best airlines flying from Chicago Midway Airport to San Juan
Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $133 | Free Cancellation | Rating 6.0 3,281 reviews | |||
| PriceFrom $174 | Free Cancellation | Rating 6.3 7,926 reviews | |||
| PriceFrom $325 | Free Cancellation | Rating 8.0 7,916 reviews | |||
| PriceFrom $342 | Free Cancellation | Rating 8.0 4,280 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to San Juan?
It is quick and easy to find Chicago to San Juan flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to San Juan that suits you.
Can I find flights from Chicago to San Juan with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to San Juan from Chicago with this policy.
How can momondo help me find flights from Chicago to San Juan?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San Juan.
I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?
Price alerts on flights to San Juan from Chicago 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.