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Cheap flights from San Juan to Chicago Midway Airport from $147

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 4/24. 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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0 bags

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Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Juan to Chicago.
Frontier Logo
6:00 am - 5:28 pmSJU-MDW
12h 28m1 stop
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
$298Frontier
Find Deal
Fri, May 9 - Mon, May 19
Frontier Logo
9:35 pm - 9:24 amSJU-MDW
12h 49m1 stop
Frontier Logo
1:26 pm - 2:49 amMDW-SJU
12h 23m1 stop
$308Frontier
Find Deal
Wed, Apr 16 - Mon, Apr 28
Frontier Logo
9:30 pm - 12:31 pmSJU-MDW
16h 01m1 stop
Frontier Logo
6:15 am - 3:22 pmMDW-SJU
8h 07m1 stop
$311Frontier
Find Deal
Wed, Apr 23 - Mon, Apr 28
Frontier Logo
4:31 pm - 11:22 pmSJU-MDW
7h 51m1 stop
Frontier Logo
2:44 pm - 11:00 pmMDW-SJU
7h 16m1 stop
$312Frontier
Find Deal
Fri, Jun 6 - Mon, Jun 9
Southwest Logo
1:00 pm - 5:20 pmSJU-MDW
5h 20mnonstop
Southwest Logo
6:35 am - 6:50 pmMDW-SJU
11h 15m1 stop
$377Southwest
Find Deal
Sat, May 10 - Sat, May 17
Delta Logo
3:34 pm - 10:22 pmSJU-MDW
7h 48m1 stop
Delta Logo
6:04 am - 4:01 pmMDW-SJU
8h 57m1 stop
$381Delta
Find Deal
Thu, May 1 - Tue, May 6
Southwest Logo
6:05 am - 12:25 pmSJU-MDW
7h 20m1 stop
Southwest Logo
5:50 am - 5:45 pmMDW-SJU
10h 55m2 stops
$388Southwest
Find Deal
Wed, May 7 - Mon, May 12
Delta Logo
7:30 am - 5:43 pmSJU-MDW
11h 13m1 stop
Delta Logo
12:48 pm - 7:48 pmMDW-SJU
6h 00m1 stop
$418Delta
Find Deal
Fri, May 9 - Sat, May 17
 Logo
1:59 am - 2:04 pmSJU-MDW
37h 05m3 stops
 Logo
2:54 pm - 3:00 pmMDW-SJU
23h 06m2 stops
Wed, May 21 - Mon, May 26
 Logo
1:59 am - 2:04 pmSJU-MDW
37h 05m3 stops
 Logo
8:04 pm - 12:54 amMDW-SJU
27h 50m3 stops
Wed, May 21 - Mon, May 26

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Apr 9
SJU2:45 amSan Juan Luis Munoz Marin Intl
7h 39m
1 stop
MDW9:24 amChicago Midway
Apr 14
MDW1:23 pmChicago Midway
7h 15m
1 stop
SJU9:38 pmSan Juan Luis Munoz Marin Intl
Frontier
May 9
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 28m
1 stop
MDW5:28 pmChicago Midway
May 19
MDW12:15 pmChicago Midway
12h 35m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
Frontier
Apr 16
SJU9:35 pmSan Juan Luis Munoz Marin Intl
12h 49m
1 stop
MDW9:24 amChicago Midway
Apr 28
MDW1:26 pmChicago Midway
12h 23m
1 stop
SJU2:49 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
May 10
SJU1:00 pmSan Juan Luis Munoz Marin Intl
5h 20m
MDW5:20 pmChicago Midway
May 17
MDW6:35 amChicago Midway
11h 15m
1 stop
SJU6:50 pmSan Juan Luis Munoz Marin Intl
Southwest
May 7
SJU6:05 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MDW12:25 pmChicago Midway
May 12
MDW5:50 amChicago Midway
10h 55m
2 stops
SJU5:45 pmSan Juan Luis Munoz Marin Intl
Southwest
May 1
SJU3:25 pmSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
MDW10:40 pmChicago Midway
May 6
MDW1:30 pmChicago Midway
8h 00m
2 stops
SJU10:30 pmSan 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

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 August 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 $610.

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 $614. 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 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $356 when searching 6 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 $244 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.

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

Best Price Found

$147

Fastest flight time

5h 00m

Direct flights

Mon, Wed, Thu and Sun
The best one-way flight to Chicago Midway Airport from San Juan in the past 72 hours is $147. The best round-trip flight deal from San Juan to Chicago Midway Airport found on momondo in the last 72 hours is $298.
The fastest flight from San Juan to Chicago Midway Airport takes 5h 00m
Direct flights go from San Juan to Chicago Midway Airport on Monday, Wednesday, Thursday and Sunday. The only airline offering direct flights is Southwest.

  • 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 5h 20m.

  • 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?

  • 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
FrontierPriceFrom $148Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,276 reviews
Search Southwest flights

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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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