Oakland to Chicago flights
The cheapest round trip we found from Oakland to Chicago is $134 (Dec 7 – 14, Nonstop), 59% below the usual $323.
OAK to CHI · Round trip · Economy · Prices per person in USD · Price found (2 days ago)
Cheapest found
Buy now or wait? We're still learning this route. We have 2 days of prices so far and need about a week to say whether to book or wait.
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $295 |
| December 2026 | $134 (cheapest month) |
| January 2027 | $323 |
| February 2027 | No fares found yet |
| March 2027 | $395 |
| April 2027 | $429 |
Cheapest dates in the next 4 months
Round trip, per person-
Dec 7 – 14 7 nights · leave Mon$134 −59% vs usual$134 −59% vs usual Book
Southwest Airlines Nonstop · 4h 00m -
Jan 6 – 12, 2027 6 nights · leave Wed$323$323 Book
Alaska Airlines 1 stop · 5h 51m -
Nov 6 – 8 2 nights · leave Fri$743 +130% vs usual$743 +130% vs usual Book
Alaska Airlines 1 stop · 5h 49m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
One Go City pass for Shedd Aquarium, Skydeck Chicago, 360 CHICAGO and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 1–5 days from $149 See pass
- Explorer Pass Pick 3–7 of 36 attractions from $109 See pass
- Essentials Pass A few top attractions, chosen as you go from $99 See pass
Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Chicago · Dec 7 – 14Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
More from Oakland
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- Ontario $101
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Flights to Chicago from other cities
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- Ontario $130 −35%
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Oakland to Chicago: questions
How much does a flight from Oakland to Chicago cost?
The cheapest round trip we have found right now is $134, leaving December 7 and returning December 14. The usual price on this route is about $323, so this fare is 59% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Oakland to Chicago?
December 2026, with round trips from $134. The most expensive month in our data is April (from $429). Based on the 5 months ahead we have prices for.
Which airports do Oakland to Chicago flights use?
Oakland airports include Metropolitan Oakland International (OAK). Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). The prices on this page cover every airport in both cities (OAK and CHI are the city codes).
About this route
We track round-trip economy fares from Oakland (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $134, departing December 7 and returning December 14 on a nonstop flight, about 59% below the usual $323. The cheapest month to fly in our data is December, from $134. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.