San Diego to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$155 is $152 (50%) below the usual $307 for San Diego → Chicago.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when San Diego → Chicago drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $307 |
| November 2026 | $155 (cheapest month) |
| December 2026 | No fares found yet |
| January 2027 | No fares found yet |
| February 2027 | No fares found yet |
| March 2027 | No fares found yet |
| April 2027 | No fares found yet |
| May 2027 | $393 |
Cheapest dates in the next 4 months
Round trip, per person-
Nov 13 – 15 2 nights · leave Fri$155 −50% vs usual$155 −50% vs usual Book
Frontier Airlines 1 stop · 5h 59m -
Oct 7 – 9 2 nights · leave Wed$307$307 Book
Frontier Airlines 1 stop · 5h 14m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Nov 13 – 15Travel insurance · EKTA Airport transfer · Kiwitaxi
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San Diego to Chicago: questions
How much is a flight from San Diego to Chicago?
The cheapest round trip we have found right now is $155, leaving November 13 and returning November 15. The usual price on this route is about $307, so this fare is 50% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from San Diego to Chicago?
November 2026, with round trips from $155. The most expensive month in our data is May (from $393). Based on the 3 months ahead we have prices for.
About this route
We track round-trip economy fares from San Diego (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $155, departing November 13 and returning November 15, about 50% below the usual $307. The cheapest month to fly in our data is November, from $155. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.