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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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Cheap round-trip flights

Frontier Logo
8:15 am - 7:36 pmSJU-MDW
12h 21m1 stop
Frontier Logo
6:15 am - 2:26 pmMDW-SJU
7h 11m1 stop
$143Frontier
Find Deal
Wed, Aug 6 - Mon, Aug 25
Frontier Logo
3:16 pm - 11:20 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
$148Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
Frontier Logo
1:11 am - 7:16 amSJU-MDW
7h 05m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$166Frontier
Find Deal
Wed, Sep 10 - Mon, Sep 15
Frontier Logo
1:06 pm - 7:16 amSJU-MDW
19h 10m1 stop
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
$212Frontier
Find Deal
Wed, Sep 17 - Mon, Sep 22
Frontier Logo
3:34 am - 8:22 pmSJU-MDW
17h 48m1 stop
Frontier Logo
9:12 pm - 8:29 pmMDW-SJU
22h 17m1 stop
$225Frontier
Find Deal
Fri, Jul 18 - Sat, Jul 26
Frontier Logo
3:21 pm - 11:27 pmSJU-MDW
9h 06m1 stop
Frontier Logo
6:15 am - 2:26 pmMDW-SJU
7h 11m1 stop
$259Frontier
Find Deal
Fri, Aug 29 - Mon, Sep 1
Delta Logo
12:50 pm - 9:44 pmSJU-MDW
9h 54m1 stop
Delta Logo
6:00 am - 4:36 pmMDW-SJU
9h 36m1 stop
$347Delta
Find Deal
Fri, Aug 29 - Tue, Sep 2
Southwest Logo
7:35 am - 3:45 pmSJU-MDW
9h 10m2 stops
Southwest Logo
12:30 pm - 10:45 pmMDW-SJU
9h 15m1 stop
$369Southwest
Find Deal
Sat, Oct 4 - Wed, Oct 8
Southwest Logo
5:30 am - 1:55 pmSJU-MDW
9h 25m1 stop
Southwest Logo
2:10 pm - 11:10 pmMDW-SJU
8h 00m1 stop
$372Southwest
Find Deal
Mon, Jul 14 - Fri, Jul 18
Southwest Logo
6:30 am - 3:50 pmSJU-MDW
10h 20m1 stop
Southwest Logo
5:15 pm - 12:55 amMDW-SJU
6h 40m1 stop
$389Southwest
Find Deal
Tue, Jul 15 - Thu, Jul 24

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Aug 6
SJU8:15 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW7:36 pmChicago Midway
Aug 25
MDW6:15 amChicago Midway
7h 11m
1 stop
SJU2:26 pmSan Juan Luis Munoz Marin Intl
Frontier
Sep 18
SJU3:16 pmSan Juan Luis Munoz Marin Intl
9h 04m
1 stop
MDW11:20 pmChicago Midway
Sep 22
MDW6:21 amChicago Midway
8h 01m
1 stop
SJU3:22 pmSan Juan Luis Munoz Marin Intl
Frontier
Sep 10
SJU1:11 amSan Juan Luis Munoz Marin Intl
7h 05m
1 stop
MDW7:16 amChicago Midway
Sep 15
MDW6:20 amChicago Midway
6h 51m
1 stop
SJU2:11 pmSan 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
Oct 4
SJU7:35 amSan Juan Luis Munoz Marin Intl
9h 10m
2 stops
MDW3:45 pmChicago Midway
Oct 8
MDW12:30 pmChicago Midway
9h 15m
1 stop
SJU10:45 pmSan Juan Luis Munoz Marin Intl
Southwest
Jul 14
SJU5:30 amSan Juan Luis Munoz Marin Intl
9h 25m
1 stop
MDW1:55 pmChicago Midway
Jul 18
MDW2:10 pmChicago Midway
8h 00m
1 stop
SJU11:10 pmSan Juan Luis Munoz Marin Intl
Southwest
Jul 15
SJU6:30 amSan Juan Luis Munoz Marin Intl
10h 20m
1 stop
MDW3:50 pmChicago Midway
Jul 24
MDW5:15 pmChicago Midway
6h 40m
1 stop
SJU12:55 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

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.

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

$76

Fastest flight time

5h 00m

Direct flights

Mon and Sun
The best one-way flight to Chicago Midway Airport from San Juan in the past 72 hours is $76. The best round-trip flight deal from San Juan to Chicago Midway Airport found on momondo in the last 72 hours is $143.
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 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 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?

  • 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 $130Free CancellationRating
5.9
3,290 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,278 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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