March is by far the best month, wherein you can get cheapest flights for San Juan to Chicago. Meanwhile, is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
Disclaimer - All the above-mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

San Juan
05:35
San Juan
Luis Munoz Marin International Airport
Tue , 14 Apr 2026

Chicago
12:10
Chicago
Chicago Midway International Airport
Tue, 14 Apr 2026

San Juan
05:05
San Juan
Luis Munoz Marin International Airport
Wed , 15 Apr 2026

Chicago
16:15
Chicago
Chicago Midway International Airport
Wed, 15 Apr 2026

San Juan
08:10
San Juan
Luis Munoz Marin International Airport
Tue , 14 Apr 2026

Chicago
13:45
Chicago
Chicago Midway International Airport
Tue, 14 Apr 2026

San Juan
14:44
San Juan
Luis Munoz Marin International Airport
Tue , 17 Mar 2026

Chicago
22:31
Chicago
Chicago Midway International Airport
Tue, 17 Mar 2026

San Juan
11:07
San Juan
Luis Munoz Marin International Airport
Tue , 17 Mar 2026

Chicago
18:13
Chicago
Chicago Midway International Airport
Tue, 17 Mar 2026

San Juan
06:15
San Juan
Luis Munoz Marin International Airport
Tue , 17 Mar 2026

Chicago
12:02
Chicago
Chicago Midway International Airport
Tue, 17 Mar 2026

San Juan
06:15
San Juan
Luis Munoz Marin International Airport
Wed , 25 Mar 2026

Chicago
12:02
Chicago
Chicago Midway International Airport
Wed, 25 Mar 2026

San Juan
16:33
San Juan
Luis Munoz Marin International Airport
Thu , 02 Apr 2026

Chicago
23:13
Chicago
Chicago Midway International Airport
Thu, 02 Apr 2026

San Juan
11:26
San Juan
Luis Munoz Marin International Airport
Sat , 04 Apr 2026

Chicago
22:29
Chicago
Chicago Midway International Airport
Sat, 04 Apr 2026

San Juan
12:32
San Juan
Luis Munoz Marin International Airport
Wed , 01 Apr 2026

Chicago
22:31
Chicago
Chicago Midway International Airport
Wed, 01 Apr 2026

San Juan
12:03
San Juan
Luis Munoz Marin International Airport
Fri , 03 Apr 2026

Chicago
22:31
Chicago
Chicago Midway International Airport
Fri, 03 Apr 2026










Flying from San Juan to Chicago has never been easier. Whether you’re planning a short business trip, a weekend getaway, or reconnecting with family and friends, Easemytrip brings you the best deals, seamless booking, and flexible options for this popular flight route. Our platform is built to help travellers like you compare flight prices, explore direct and connecting options, and find the perfect departure time — all within a few clicks.
The air route between San Juan to Chicago is one of the most frequently travelled, offering reliable services from top airlines and excellent connectivity between Luis Munoz Marin International Airport (SJU) and Chicago Midway International Airport (MDW). You can expect a flight distance of approximately 3313 km, and most direct services cover it in around 07:59.
Let’s take a closer look at everything you need to know before booking your flight from San Juan to Chicago.
| Flight Details | Information |
|---|---|
| Route Distance | 3313 km |
| Average Flight Time | 07:59 hrs |
| Departure Airport | Luis Munoz Marin International Airport (SJU) |
| Arrival Airport | Chicago Midway International Airport (MDW) |
| Cabin Classes Available | Economy Class, Premium Economy, Business Class, First Class |
| Direct Flights | NO |
| Common Airlines | Southwest, Delta Airlines, Frontier Airlines, Cape Air |
The route is serviced regularly by both full-service and budget airlines, catering to all types of travellers — from those looking for no-frills budget options to those preferring business and first-class comfort. If you're flying for business, early morning weekday flights are a great choice, while leisure travellers often opt for weekend and evening departures.