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Cheap flights from San Juan to Chicago from $107

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 12/20. 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

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Frontier Logo
3:55 am - 9:04 pmSJU-MDW
19h 09m1 stop
Frontier Logo
6:00 am - 1:37 amMDW-SJU
17h 37m1 stop
$195Frontier
Find Deal
Fri, Dec 19 - Sun, Jan 4
Frontier Logo
7:09 pm - 5:15 pmSJU-MDW
24h 06m1 stop
Frontier Logo
5:30 pm - 9:12 pmMDW-SJU
25h 42m1 stop
$206Frontier
Find Deal
Mon, Nov 24 - Wed, Nov 26
Frontier Logo
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
3:10 pm - 2:50 amMDW-SJU
9h 40m1 stop
$211Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
4:21 pm - 10:12 pmSJU-MDW
7h 51m1 stop
Frontier Logo
6:00 am - 12:59 pmMDW-SJU
28h 59m1 stop
$212Frontier
Find Deal
Thu, Dec 18 - Fri, Jan 9
Frontier Logo
3:54 am - 10:12 pmSJU-MDW
44h 18m2 stops
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$217Frontier
Find Deal
Fri, Dec 26 - Sat, Jan 3
Frontier Logo
4:16 pm - 5:38 pmSJU-MDW
27h 22m1 stop
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$219Frontier
Find Deal
Wed, Dec 24 - Sat, Jan 3
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
2:59 pm - 7:50 pmMDW-SJU
26h 51m1 stop
$221Multiple Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
3:54 am - 1:21 pmSJU-MDW
11h 27m2 stops
Multiple Airlines Logo
6:00 am - 1:37 amMDW-SJU
17h 37m1 stop
$223Multiple Airlines
Find Deal
Fri, Dec 19 - Sun, Jan 4
Frontier Logo
7:35 am - 10:12 pmSJU-MDW
16h 37m2 stops
Frontier Logo
6:12 am - 12:37 amMDW-SJU
16h 25m1 stop
$225Frontier
Find Deal
Sat, Dec 27 - Thu, Jan 1
Frontier Logo
3:55 am - 1:47 pmSJU-MDW
11h 52m1 stop
Frontier Logo
3:10 pm - 1:50 amMDW-SJU
9h 40m1 stop
$226Frontier
Find Deal
Thu, Mar 5 - Tue, Mar 10

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Dec 19
SJU3:55 amSan Juan Luis Munoz Marin Intl
19h 09m
1 stop
MDW9:04 pmChicago Midway
Jan 4
MDW6:00 amChicago Midway
17h 37m
1 stop
SJU1:37 amSan Juan Luis Munoz Marin Intl
$195
Find similar
Frontier
Nov 22
SJU7:10 amSan Juan Luis Munoz Marin Intl
30h 32m
1 stop
MDW11:42 amChicago Midway
Nov 26
MDW5:57 pmChicago Midway
13h 43m
1 stop
SJU9:40 amSan Juan Luis Munoz Marin Intl
$198
Find similar
Frontier
Nov 24
SJU7:09 pmSan Juan Luis Munoz Marin Intl
24h 06m
1 stop
MDW5:15 pmChicago Midway
Nov 26
MDW5:30 pmChicago Midway
25h 42m
1 stop
SJU9:12 pmSan Juan Luis Munoz Marin Intl
$206
Find similar

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Jan 16
SJU7:00 amSan Juan Luis Munoz Marin Intl
13h 35m
1 stop
MDW6:35 pmChicago Midway
Jan 19
MDW1:35 pmChicago Midway
8h 30m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
$245
Find similar
Southwest
Jan 30
SJU5:40 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW12:30 pmChicago Midway
Feb 4
MDW8:25 amChicago Midway
6h 40m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
$256
Find similar
Southwest
Feb 27
SJU6:30 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW1:20 pmChicago Midway
Mar 2
MDW6:10 amChicago Midway
13h 40m
1 stop
SJU9:50 pmSan Juan Luis Munoz Marin Intl
$257
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Juan to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from San Juan to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/19

3:55 am-9:04 pm

1 stop19h 09m

Chicago Midway

Sun 1/4

6:00 am-1:37 am

1 stop17h 37m

$195

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 11/24

7:09 pm-5:15 pm

1 stop24h 06m

Chicago Midway

Wed 11/26

5:30 pm-9:12 pm

1 stop25h 42m

$206

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

4:31 pm-10:12 pm

1 stop7h 41m

Chicago Midway

Mon 12/8

3:10 pm-2:50 am

1 stop9h 40m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/18

4:21 pm-10:12 pm

1 stop7h 51m

Chicago Midway

Fri 1/9

6:00 am-12:59 pm

1 stop28h 59m

$212

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/26

3:54 am-10:12 pm

2 stops44h 18m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

4:16 pm-5:38 pm

1 stop27h 22m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$219

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/11

10:42 am-9:53 pm

1 stop13h 11m

Chicago Midway

Sat 12/13

2:59 pm-7:50 pm

1 stop26h 51m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/19

3:54 am-1:21 pm

2 stops11h 27m

Chicago Midway

Sun 1/4

6:00 am-1:37 am

1 stop17h 37m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 12/27

7:35 am-10:12 pm

2 stops16h 37m

Chicago Midway

Thu 1/1

6:12 am-12:37 am

1 stop16h 25m

$225

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

3:55 am-1:47 pm

1 stop11h 52m

Chicago Midway

Tue 3/10

3:10 pm-1:50 am

1 stop9h 40m

$226

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $294. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan during the month February is also very affordable. Most momondo users find prices during this month for around $325.

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 $580. 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

What cabin class options are available on San Juan to Chicago Midway flights?

There is only 1 cabin class 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

Fastest flight time

5h 15m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 5h 15m
Direct flights go from San Juan to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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 7h 41m.

  • 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
5.8
3,114 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,236 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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