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Cheap flights from San Juan to Chicago from $95

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 3/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:31 pm - 4:16 pm
SJU
-
MDW
25h 45m
2 stops
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$198Multiple Airlines
Wed, Feb 25 - Sun, Mar 1
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$202Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Frontier Logo
6:00 am - 9:03 pm
MDW
-
SJU
14h 03m
1 stop
$205Frontier
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Multiple Airlines Logo
6:00 am - 5:58 pm
MDW
-
SJU
10h 58m
1 stop
$206Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
4:16 pm - 10:37 pm
SJU
-
MDW
8h 21m
1 stop
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
$208Multiple Airlines
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
Frontier Logo
7:30 am - 12:43 am
MDW
-
SJU
15h 13m
1 stop
$212Frontier
Fri, Feb 20 - Thu, Feb 26
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$217Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
9:51 pm - 10:12 am
MDW
-
SJU
11h 21m
1 stop
$220Frontier
Wed, Mar 4 - Mon, Mar 9
Frontier Logo
1:11 pm - 10:19 pm
SJU
-
MDW
10h 08m
1 stop
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
$223Frontier
Wed, Apr 8 - Fri, Apr 10
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
$229Frontier
Wed, Feb 25 - Mon, Mar 2

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
Apr 16
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 14m
1 stop
MDW4:29 pmChicago Midway
Apr 22
MDW12:53 pmChicago Midway
6h 31m
1 stop
SJU8:24 pmSan Juan Luis Munoz Marin Intl
$246
Delta
Apr 18
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 10m
1 stop
MDW4:25 pmChicago Midway
Apr 21
MDW10:43 amChicago Midway
8h 41m
1 stop
SJU8:24 pmSan Juan Luis Munoz Marin Intl
$256
Delta
Feb 24
SJU3:55 pmSan Juan Luis Munoz Marin Intl
8h 38m
1 stop
MDW10:33 pmChicago Midway
Mar 10
MDW10:45 amChicago Midway
8h 33m
1 stop
SJU8:18 pmSan Juan Luis Munoz Marin Intl
$276

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 10
MDW6:00 amChicago Midway
7h 08m
1 stop
SJU2:08 pmSan Juan Luis Munoz Marin Intl
$202
Frontier
Mar 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
Mar 9
MDW6:00 amChicago Midway
14h 03m
1 stop
SJU9:03 pmSan Juan Luis Munoz Marin Intl
$205
Frontier
Feb 20
SJU3:53 amSan Juan Luis Munoz Marin Intl
13h 02m
1 stop
MDW2:55 pmChicago Midway
Feb 26
MDW7:30 amChicago Midway
15h 13m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
$212

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 February 11, 2026.
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

Wed 2/25

4:31 pm-4:16 pm

2 stops25h 45m

Chicago Midway

Sun 3/1

6:15 am-2:09 am

1 stop17h 54m

$198

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

6:00 am-2:08 pm

1 stop7h 08m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/9

6:00 am-9:03 pm

1 stop14h 03m

$205

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/9

6:00 am-5:58 pm

1 stop10h 58m

$206

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

4:16 pm-10:37 pm

1 stop8h 21m

Chicago Midway

Mon 3/2

2:19 pm-6:58 pm

2 stops26h 39m

$208

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/20

3:53 am-2:55 pm

1 stop13h 02m

Chicago Midway

Thu 2/26

7:30 am-12:43 am

1 stop15h 13m

$212

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/11

6:00 am-2:08 pm

1 stop7h 08m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 3/4

3:53 am-2:26 pm

1 stop12h 33m

Chicago Midway

Mon 3/9

9:51 pm-10:12 am

1 stop11h 21m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/8

1:11 pm-10:19 pm

1 stop10h 08m

Chicago Midway

Fri 4/10

2:56 pm-12:52 am

1 stop8h 56m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/25

3:53 am-2:26 pm

1 stop12h 33m

Chicago Midway

Mon 3/2

6:00 am-3:02 pm

1 stop7h 02m

$229

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 $302. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan during the month November is also very affordable. Most momondo users find prices during this month for around $336.

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

4h 50m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 4h 50m
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 4h 50m.

  • 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
SouthwestPriceFrom $419Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
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Portage
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Schererville
Valparaiso
Munster
Crown Point
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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