SJU - MDW

$126 Find Cheap Flights from San Juan to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Juan to Midway departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$226
Typical prices: $288-$501
Southwest
Wed 9/30Mon 10/5
SJU - MDW • 2 stops
Cheapest one-way
$124
Typical prices: $233-$358
JetBlue
Thu 8/27
SJU - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between San Juan and Midway. You'll need at least 1 connection.
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Top layover airports
Atlanta (ATL)
Cheapest • Avg $284 (round-trip)
Orlando (MCO)
Shortest trip • 7h 05m (one-way)
Insights
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When to travel
March
Cheapest • 100% price drop
November
Most popular
Good to know
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Juan to Midway (SJU-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Juan to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Juan to Midway

Wed, Sep 30 - Mon, Oct 5
Southwest Logo
5:15 am - 12:05 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 50m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
2:15 pm - 12:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 05m1 stop Orlando
$226Southwest
Wed, Sep 30 - Mon, Oct 5
Southwest Logo
8:20 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 25m1 stop Orlando
Southwest Logo
2:15 pm - 12:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 05m1 stop Orlando
$226Southwest
Fri, Sep 18 - Tue, Sep 22
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$246Southwest
Fri, Sep 18 - Tue, Sep 22
Southwest Logo
2:35 pm - 9:35 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 00m1 stop Orlando
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$246Southwest
Fri, Sep 18 - Mon, Sep 28
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
11:15 am - 10:15 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 00m1 stop Orlando
$256Southwest
Fri, Sep 18 - Mon, Sep 28
Southwest Logo
6:30 am - 3:35 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
10h 05m1 stop Orlando
Southwest Logo
11:15 am - 10:15 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 00m1 stop Orlando
$256Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
2:35 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
8:05 pm - 9:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$266Southwest
Wed, Oct 14 - Sun, Oct 18
Southwest Logo
8:15 am - 7:20 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
12h 05m2 stops Fort Lauderdale Pittsburgh
Southwest Logo
5:25 pm - 1:25 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 00m1 stop Orlando
$266Southwest
Mon, Oct 19 - Thu, Oct 22
JetBlue Logo
8:50 pm - 8:25 amSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
12h 35m1 stop Orlando
JetBlue Logo
8:40 pm - 9:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
$292JetBlue
Wed, Oct 21 - Wed, Oct 28
JetBlue Logo
8:15 am - 7:50 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
12h 35m1 stop Fort Lauderdale
JetBlue Logo
4:40 pm - 11:45 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 05m1 stop Orlando
$292JetBlue
Booking Insights

KAYAK's insights & trends for San Juan to Midway flights

Get data-powered insights and trends into flights from San Juan to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport departing in September.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport usually cost between $266 and $347 in September.
The lowest price found in the past 5 days was $256 on Southwest (Sep 25-Sep 29).

What’s the cheapest day of the week to fly from San Juan to Chicago Midway Airport?

The average price of all round-trip flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

For San Juan to Chicago Midway Airport, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to San Juan, the best deals are generally found on Sunday, with Saturday being the most expensive.

What is the cheapest month to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are February and January, where the average cost of round-trip tickets is $726 and $540 respectively.

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Good to know

Low season

August

Cheapest flight

$126
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from San Juan to Chicago Midway Airport

When to book flights from San Juan to Midway

Are your dates flexible? Find out the best times to travel from San Juan to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Juan to Chicago Midway Airport flights

  • What is the cheapest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport was $124 for a one-way ticket and $226 for a round-trip.

  • Do I need a passport to fly between San Juan and Chicago Midway Airport?

    A passport is required to fly from San Juan to Chicago Midway Airport.

  • Which airports will I be using when flying from San Juan to Chicago Midway Airport?

    When flying out of San Juan you will be using San Juan Luis Munoz Marin Intl. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from San Juan to Chicago Midway Airport?

    Only Delta offers inflight Wi-Fi service on the San Juan to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from San Juan to Chicago Midway Airport?

    The Airbus A321neo is the aircraft model that flies most regularly on the San Juan to Chicago Midway Airport flight route.

  • How does KAYAK find such low prices on flights from San Juan to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Juan to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Juan to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Juan is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Juan to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to San Juan with another airline. Booking your flights between San Juan and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Juan to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from San Juan up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $279 or less one-way and $552 or less round-trip.

Everything you need to know for your flight from San Juan to Midway

Information on your arrival and departure airports

San Juan (SJU)
Midway (MDW)