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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 4/15. 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.
Frontier Logo
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$202Frontier
Thu, Apr 30 - Mon, May 4
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
$223Frontier
Fri, May 8 - Mon, May 11
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
$233Frontier
Thu, May 14 - Mon, May 18
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
$235Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:06 pm
MDW
-
SJU
27h 52m
1 stop
$237Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:08 am - 6:13 pm
SJU
-
MDW
16h 05m
1 stop
Frontier Logo
9:51 pm - 10:45 pm
MDW
-
SJU
23h 54m
1 stop
$242Frontier
Tue, Mar 17 - Mon, Mar 23
Delta Logo
6:15 am - 4:26 pm
SJU
-
MDW
11h 11m
1 stop
Delta Logo
10:41 am - 8:24 pm
MDW
-
SJU
8h 43m
1 stop
$246Delta
Sat, Apr 18 - Tue, Apr 21
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m
1 stop
Frontier Logo
11:19 am - 2:03 am
MDW
-
SJU
13h 44m
1 stop
$249Frontier
Thu, Mar 5 - Tue, Mar 17
Frontier Logo
6:33 pm - 9:58 pm
SJU
-
MDW
28h 25m
1 stop
Frontier Logo
5:30 am - 1:26 pm
MDW
-
SJU
6h 56m
1 stop
$250Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
6:39 pm - 5:48 pm
SJU
-
MDW
24h 09m
1 stop
Frontier Logo
4:33 pm - 2:03 am
MDW
-
SJU
8h 30m
1 stop
$259Frontier
Tue, Mar 24 - Tue, Mar 31

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
May 1
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
May 4
MDW6:00 amChicago Midway
7h 13m
1 stop
SJU2:13 pmSan Juan Luis Munoz Marin Intl
$202
Frontier
May 8
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 11
MDW6:00 amChicago Midway
7h 08m
1 stop
SJU2:08 pmSan Juan Luis Munoz Marin Intl
$223
Frontier
Feb 26
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
Mar 1
MDW6:15 amChicago Midway
17h 54m
1 stop
SJU2:09 amSan Juan Luis Munoz Marin Intl
$230

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
Apr 18
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 11m
1 stop
MDW4:26 pmChicago Midway
Apr 21
MDW10:41 amChicago Midway
8h 43m
1 stop
SJU8:24 pmSan Juan Luis Munoz Marin Intl
$246
Delta
Mar 18
SJU7:30 amSan Juan Luis Munoz Marin Intl
10h 52m
1 stop
MDW5:22 pmChicago Midway
Mar 31
MDW6:00 amChicago Midway
9h 18m
1 stop
SJU4:18 pmSan Juan Luis Munoz Marin Intl
$266
Delta
Feb 24
SJU3:55 pmSan Juan Luis Munoz Marin Intl
8h 38m
1 stop
MDW10:33 pmChicago Midway
Mar 10
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJU11:15 pmSan Juan Luis Munoz Marin Intl
$316

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 23, 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

Thu 4/30

3:21 am-10:28 am

1 stop8h 07m

Chicago Midway

Mon 5/4

6:00 am-2:13 pm

1 stop7h 13m

$202

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

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/14

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/18

6:00 am-2:08 pm

1 stop7h 08m

$233

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

$235

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

9:14 am-2:06 pm

1 stop27h 52m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/17

3:08 am-6:13 pm

1 stop16h 05m

Chicago Midway

Mon 3/23

9:51 pm-10:45 pm

1 stop23h 54m

$242

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 4/18

6:15 am-4:26 pm

1 stop11h 11m

Chicago Midway

Tue 4/21

10:41 am-8:24 pm

1 stop8h 43m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Tue 3/17

11:19 am-2:03 am

1 stop13h 44m

$249

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:33 pm-9:58 pm

1 stop28h 25m

Chicago Midway

Mon 4/13

5:30 am-1:26 pm

1 stop6h 56m

$250

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/24

6:39 pm-5:48 pm

1 stop24h 09m

Chicago Midway

Tue 3/31

4:33 pm-2:03 am

1 stop8h 30m

$259

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

5h 10m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 5h 10m
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 5h 10m.

  • 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
4,300 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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Munster
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Porter
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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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