Prices may change. Select and confirm the full itinerary with the booking provider. Dates can differ between airport cards.
A great San Juan trip starts with a fare worth finding. Compare the latest samples below, then join our upcoming free newsletter to get standout Chicago flight finds in your inbox.
Same airports & dates. Each provider checks its own current prices.
ORD → SJU · Nov 6–Nov 13
Search fare; select your return flight to confirm.
Spend more on being in San Juan, and less on getting there. These are real examples from our research—the reason it pays to keep an eye on the fares.
$227 for Nov 6–Nov 13, 2026, compared with $755 for Dec 28–Jan 4, 2027.
12 seven-night date pairs from ORD to the same arrival-airport set (SJU). Lowest returned fare per date pair; checks within 24 hours. Airlines, stops and ticket conditions can differ. A travel-date comparison, not a booking-time prediction.
Explore the cheaper date samples ↗The same dated search ranged from $208 to $410 across 61 historical price observations.
ORD → SJU · Nov 6–Nov 13, 2026. Google Flights history covers Jul 29, 2026–Sep 27, 2026. The percentage is the low below the high. This does not prove when you should book or what subscribers will save.
See the price history ↗ORD → SJU · Nov 6–Nov 13, 2026. Recorded Sep 27, 2026.
Our archive starts Sep 27, 2026 and contains 233 seven-night fare observations for this route. Search fare; return may require confirmation. This is our record, not an industry-wide all-time low or a current offer.
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Same dates: Nov 6–Nov 13. Same arrival airports: SJU.
1 stop outbound
2 stops outbound
$55 separates the lowest and highest airport sample for these dates. These are search-result fares for seven-night trips. Flight times, stops and baggage can differ. Ground transport is excluded.
Across 12 matched date pairs in this sample, ORD had the lowest airport fare 11 time(s); MDW had the lowest airport fare 1 time(s). Ties count for each airport. This describes the sampled dates only.
A cheaper ticket can come with a pricier ride. Add your own round-trip transport estimate to the matched fares.
Flight sample $311
$311fare + transportFlight sample $377
$377fare + transportAdd your transport estimates to compare your total.
One adult, economy, USD. The two fares use identical dates and arrival-airport sets, checked within 24 hours. Transport starts at $0 because we don’t know your starting point. Baggage and other extras are excluded. Prices and itineraries can differ.
ORD → SJU, Feb 18. Nonstop.
Across 24 seven-night airport/date searches. Includes connecting carriers.
Lowest: $227, Nov 6–Nov 13 from ORD.
ORD, MDW in these outbound results. This is not a full schedule.
Derived from the current seven-night observations on this page. Outbound times describe the outbound journey only; fare amounts are round-trip search results. See sources and coverage.
Lowest fare in each sampled departure month. Seven-night trips only.
Swipe to see more months →
Tap a bar to see the dates, airports and check time behind that sample.
| Departure month | Lowest sample | Date pairs |
|---|---|---|
| 2026-10 | $311 | 1 |
| 2026-11 | $227 | 1 |
| 2026-12 | $282 | 2 |
| 2027-01 | $250 | 1 |
| 2027-02 | $252 | 1 |
| 2027-03 | $360 | 1 |
| 2027-04 | $320 | 1 |
| 2027-05 | $256 | 1 |
| 2027-06 | $252 | 2 |
| 2027-07 | $381 | 1 |
Sampled dates, not a complete fare calendar. Each month can have different date coverage. This chart describes future travel dates, not past price movements.
Prices checked within seven days. Use the filters to find a trip that fits.
| Dates / airports | Airline / outbound | Round trip | Check price |
|---|---|---|---|
| Nov 6–Nov 13ORD → SJU · 7 nights |  American1 stop · 15h 29m | $227Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SJU · 7 nights | American1 stop · 13h 28m | $250Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SJU · 7 nights | American2 stops · 15h 39m | $250Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25ORD → SJU · 7 nights | American2 stops · 17h 10m | $252Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8ORD → SJU · 7 nights | AmericanNonstop · 4h 39m | $252Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13ORD → SJU · 7 nights | American2 stops · 17h 31m | $256Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → SJU · 7 nights |  Frontier1 stop · 21h 35m | $261Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SJU · 7 nights |  United1 stop · 7h 7m | $271Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13MDW → SJU · 7 nights |  Southwest2 stops · 8h 10m | $282Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9MDW → SJU · 7 nights | Southwest2 stops · 9h 30m | $282Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13MDW → SJU · 7 nights | Southwest1 stop · 7h 10m | $282Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → SJU · 7 nights |  JetBlue1 stop · 9h 0m | $288Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → SJU · 7 nights | United1 stop · 9h 47m | $288Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8ORD → SJU · 7 nights | United1 stop · 8h 29m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SJU · 7 nights | UnitedNonstop · 4h 44m | $304Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9MDW → SJU · 7 nights | Frontier1 stop · 10h 39m | $308Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → SJU · 7 nights | Frontier1 stop · 15h 53m | $308Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18ORD → SJU · 7 nights | Frontier1 stop · 18h 17m | $311Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SJU · 7 nights | AmericanNonstop · 4h 40m | $316Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25ORD → SJU · 7 nights | American1 stop · 8h 26m | $316Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30MDW → SJU · 7 nights | Southwest1 stop · 6h 20m | $320Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17ORD → SJU · 7 nights | American1 stop · 12h 49m | $320Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → SJU · 7 nights | UnitedNonstop · 4h 44m | $349Return also checkedChecked Sep 27 | Google Skyscanner ↗ItineraryORD → SJU SJU → ORD |
| Mar 15–Mar 22ORD → SJU · 7 nights | AmericanNonstop · 4h 39m | $360Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25MDW → SJU · 7 nights | Southwest1 stop · 7h 50m | $372Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18MDW → SJU · 7 nights | Frontier1 stop · 8h 42m | $377Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30ORD → SJU · 7 nights | AmericanNonstop · 4h 58m | $381Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17MDW → SJU · 7 nights | Southwest2 stops · 8h 10m | $390Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13MDW → SJU · 7 nights | Southwest2 stops · 12h 30m | $402Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4ORD → SJU · 7 nights | AmericanNonstop · 4h 39m | $436Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22MDW → SJU · 7 nights | Southwest2 stops · 14h 40m | $506Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8MDW → SJU · 7 nights | Southwest1 stop · 11h 5m | $557Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4ORD → SJU · 7 nights | American1 stop · 13h 37m | $755Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4MDW → SJU · 7 nights | Southwest2 stops · 12h 25m | $796Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4MDW → SJU · 7 nights |  Delta1 stop · 6h 45m | $1,152Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30MDW → SJU · 7 nights | Delta1 stop · 6h 45m | $1,443Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
No samples match these filters. Try another airport or trip length.
Prices can change. Cabin baggage and checked bags are not assumed included. Confirm the complete itinerary, airline fare rules and final price on the booking site.
ORD → SJU · Nov 6–Nov 13, 2026
| Observation date | Price |
|---|---|
| Jul 29, 2026 | $396 |
| Jul 30, 2026 | $339 |
| Jul 31, 2026 | $339 |
| Aug 1, 2026 | $405 |
| Aug 2, 2026 | $405 |
| Aug 3, 2026 | $405 |
| Aug 4, 2026 | $405 |
| Aug 5, 2026 | $310 |
| Aug 6, 2026 | $310 |
| Aug 7, 2026 | $326 |
| Aug 8, 2026 | $359 |
| Aug 9, 2026 | $359 |
| Aug 10, 2026 | $301 |
| Aug 11, 2026 | $301 |
| Aug 12, 2026 | $321 |
| Aug 13, 2026 | $316 |
| Aug 14, 2026 | $321 |
| Aug 15, 2026 | $367 |
| Aug 16, 2026 | $410 |
| Aug 17, 2026 | $410 |
| Aug 18, 2026 | $390 |
| Aug 19, 2026 | $398 |
| Aug 20, 2026 | $372 |
| Aug 21, 2026 | $372 |
| Aug 22, 2026 | $372 |
| Aug 23, 2026 | $372 |
| Aug 24, 2026 | $222 |
| Aug 25, 2026 | $222 |
| Aug 26, 2026 | $226 |
| Aug 27, 2026 | $226 |
| Aug 28, 2026 | $226 |
| Aug 29, 2026 | $226 |
| Aug 30, 2026 | $226 |
| Aug 31, 2026 | $226 |
| Sep 1, 2026 | $226 |
| Sep 2, 2026 | $226 |
| Sep 3, 2026 | $226 |
| Sep 4, 2026 | $226 |
| Sep 5, 2026 | $226 |
| Sep 6, 2026 | $226 |
| Sep 7, 2026 | $226 |
| Sep 8, 2026 | $222 |
| Sep 9, 2026 | $226 |
| Sep 10, 2026 | $226 |
| Sep 11, 2026 | $243 |
| Sep 12, 2026 | $243 |
| Sep 13, 2026 | $243 |
| Sep 14, 2026 | $235 |
| Sep 15, 2026 | $218 |
| Sep 16, 2026 | $221 |
| Sep 17, 2026 | $209 |
| Sep 18, 2026 | $229 |
| Sep 19, 2026 | $229 |
| Sep 20, 2026 | $229 |
| Sep 21, 2026 | $229 |
| Sep 22, 2026 | $208 |
| Sep 23, 2026 | $227 |
| Sep 24, 2026 | $227 |
| Sep 25, 2026 | $227 |
| Sep 26, 2026 | $208 |
| Sep 27, 2026 | $227 |
Google Flights price history returned through Scrapingdog for the dates and settings above. It is not a destination-wide average or a prediction. Source checked Sep 27, 2026.
Airport context and source-backed details to help you compare the whole journey.
San Juan, Puerto Rico · Airport coordinates 18.439, -66.002
Lowest sample to SJU: $227 round trip from ORD, Nov 6–Nov 13. Different arrival airports may use different dates.
Airport informationThis page searches SJU — Luis Munoz Marin International Airport. Airport coverage follows the destination city market in the passenger dataset, with minor airports excluded. Always check the airport code on both legs: a city search can include different arrival airports, and the cheapest option may not be closest to where you are staying.
Read the sourceBTS recorded 241,365 scheduled passengers departing O’Hare and Midway for this destination city market from 2025-07 to 2026-06. That puts it at number 51 in our selected ranking. These are historical on-flight market passengers, not unique travelers, current flight frequencies or a measure of search popularity.
Read the sourceThe airport reference places Luis Munoz Marin International Airport in San Juan, Puerto Rico, at 18.439°, -66.002°. Use the airport’s official information to plan your arrival and return journey. Our fare table compares air travel only; ground transfers, luggage and accommodation can change the total trip budget.
Read the sourceKeep an eye on the whole travel budget, from your first night to your last mile.
Compare places to stay in San Juan. Add your dates, check the location, and compare the final total and cancellation terms.
Explore San Juan stays ↗Booking.com · choose your travel datesPlanning a drive beyond San Juan? Compare rental cars, mileage, deposits and pickup hours. City-only trip? Public transit may suit you better.
Compare rental cars ↗Discover Cars · enter SJU and your datesThese are planning links, not priced offers. Hotel and car availability is checked by the provider. We currently receive no commission from these links.
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The lowest seven-night round-trip search fare in our archive is $227, recorded Sep 27, 2026 for ORD to SJU, Nov 6–Nov 13, 2026. Our route archive starts Sep 27, 2026. This is our observed record, not an industry-wide all-time low, a verified booking price or a current offer.
Our lowest current seven-night sample is $227 round trip for one adult in economy, from ORD to SJU, Nov 6–Nov 13, 2026. It was checked Sep 27, 2026. This is a dated search result, not a guaranteed ticket price; confirm the return and full fare conditions before paying.
For the matched Nov 6–Nov 13, 2026 search, ORD had the lowest sample at $227. The highest and lowest airport fares were $55 apart. That applies to those dates and settings only. Try other matched dates and add your own ground transport cost in the airport calculator above.
The current sample includes a nonstop outbound from ORD to SJU on Jun 1, 2027, with a round-trip search fare of $252. Check the return direction separately: a nonstop outbound does not guarantee a nonstop return.
The travel-period chart compares only the dates we sampled. It cannot establish the cheapest month of the year. Start with a promising sampled period, then check nearby dates with the same trip length. The separate history chart tracks one specific search over time; it is not a travel calendar.
This destination market includes Luis Munoz Marin International Airport (SJU). Check the exact arrival code on the fare you choose, then compare the onward journey to your accommodation. The arrival section links airport information and our source-backed planning notes.
Not necessarily. The buttons open separate searches with matching airports and dates when a dated sample is available. Providers can show different airlines, sellers, baggage rules and live prices. The sampled Google Flights price is never a Skyscanner quote.
Do not assume bags are included unless the provider explicitly confirms them. Our research shows flight search fares; the accommodation and rental-car links are separate planning tools. Compare the final total, cancellation terms and location before booking any part of the trip.
Answers use the dated research and sources on this page. Read our flight-saving field notes for a broader planning checklist.
Get our best flight finds in your inbox ↗This page contains 232 current search-result observations across 24 airport/date searches. Route research is compiled by the Chicago Flight Research desk from the sources below.
Destination photography: photographer, source and reuse license. Airline logos identify the carriers shown in results; no partnership is implied.
BTS demand period: 2025-07 to 2026-06. Searches use one adult, economy, USD and the US market. We do not sell tickets, guarantee fares, or infer baggage inclusions. Read the full methodology
