CHI - OAK

$110 Find Cheap Flights from Chicago to Oakland - Compare and Save

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Everything you should know

Cheapest round-trip
$228
Typical prices: $303-$530
Frontier
Tue 10/30Fri 11/2
ORD - OAK • 1 stop
Cheapest non-stop
$237
Typical prices: $301-$557
Southwest
Sat 11/10Wed 11/14
MDW - OAK • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 38m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Avoid delays
Most punctual • 68% on-time
Best time • Fewest delays
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $334 (round-trip)
Shortest trip • 6h 18m (one-way)
Insights
Insights
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Expert advice
Flight Deals

Cheap Flights from Chicago to Oakland (CHI-OAK)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Oakland

Fri, Oct 30 - Mon, Nov 2
Frontier Logo
5:15 pm - 11:53 amORD  Chicago O'Hare Intl-OAK Oakland
20h 38m1 stop Las Vegas Harry Reid Intl
Frontier Logo
10:18 am - 5:13 amOAK  Oakland-ORD Chicago O'Hare Intl
16h 55m1 stop Las Vegas Harry Reid Intl
$228Frontier
Tue, Nov 10 - Sat, Nov 14
Southwest Logo
8:45 pm - 11:30 pmMDW  Chicago Midway-OAK Oakland
4h 45mnonstop
Southwest Logo
11:50 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 05mnonstop
$237Southwest
Tue, Oct 20 - Sat, Oct 24
Southwest Logo
8:35 pm - 11:20 pmMDW  Chicago Midway-OAK Oakland
4h 45mnonstop
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
$237Southwest
Fri, Oct 2 - Mon, Oct 5
Frontier Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
Frontier Logo
10:17 am - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
17h 21m1 stop Las Vegas Harry Reid Intl
$238Frontier
Fri, Oct 9 - Mon, Oct 12
Southwest Logo
9:30 pm - 12:15 amMDW  Chicago Midway-OAK Oakland
4h 45mnonstop
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
$247Southwest
Mon, Sep 21 - Fri, Sep 25
Multiple Airlines Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
6:48 am - 7:21 pmOAK  Oakland-ORD Chicago O'Hare Intl
10h 33m1 stop San Diego
$249Multiple Airlines
Tue, Nov 10 - Wed, Nov 11
Alaska Airlines Logo
7:20 am - 2:10 pmORD  Chicago O'Hare Intl-OAK Oakland
8h 50m1 stop San Diego
Alaska Airlines Logo
10:00 am - 6:59 pmOAK  Oakland-ORD Chicago O'Hare Intl
6h 59m1 stop San Diego
$277Alaska Airlines
Thu, Oct 1 - Tue, Nov 3
Alaska Airlines Logo
7:20 am - 2:33 pmORD  Chicago O'Hare Intl-OAK Oakland
9h 13m1 stop San Diego
Alaska Airlines Logo
6:13 pm - 1:17 pmOAK  Oakland-ORD Chicago O'Hare Intl
17h 04m1 stop San Diego
$277Alaska Airlines
Tue, Oct 20 - Wed, Nov 4
Delta Logo
7:15 pm - 11:56 pmORD  Chicago O'Hare Intl-OAK Oakland
6h 41m1 stop Salt Lake City
Delta Logo
12:41 pm - 10:05 pmOAK  Oakland-ORD Chicago O'Hare Intl
7h 24m1 stop Salt Lake City
$277Delta
Wed, Oct 14 - Wed, Oct 21
Delta Logo
7:15 pm - 11:56 pmORD  Chicago O'Hare Intl-OAK Oakland
6h 41m1 stop Salt Lake City
Delta Logo
12:41 pm - 10:05 pmOAK  Oakland-ORD Chicago O'Hare Intl
7h 24m1 stop Salt Lake City
$277Delta
Booking Insights

Price, demand and travel trends for Chicago to Oakland flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to Oakland with more confidence.

How much is a round-trip flight from Chicago to Oakland?

Round-trip flights from Chicago to Oakland start at $228. Prices are below average for this route right now, with typical round-trip fares ranging from $303 to $530. The lowest price found in the past 5 days was $228 on Frontier.

What is the cheapest Chicago to Oakland flight route?

There's little price difference between Chicago to Oakland routes. They average around $399 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to Oakland?

Saturday is the cheapest day of the week to fly from Chicago to Oakland, it is 13% cheaper than the average day. Sunday is the most expensive day with flight prices 26% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago to Oakland?

  • April is the cheapest month to fly from Chicago to Oakland at $310 round-trip.
  • November ($518) and June ($480) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 67% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Expert advice

Expert advice for your flight from Chicago to Oakland

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Gabriel Leigh

Gabriel Leigh

Expert on OAK

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Key details for Chicago to Oakland flights

Low season

December

Cheapest flight

$110
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Chicago O'Hare Intl Airport to Oakland

When to book flights from Chicago to Oakland

Are your dates flexible? Find out the best times to travel from Chicago to Oakland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to Oakland flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Are there lounges in O'Hare International Airport (ORD) where passengers can await their departures?

    There are various lounge facilities within the different terminals at the airport. The main lounge in Terminal 1 is the United Club by United airlines which has four lounges: near Gates C16, C18, B18, and B6. The other is the Delta Sky Club in Terminal 2, where United Club also has a place on the grid. There are also multiple other lounge facilities in Terminal 3, mainly occupied by American Airlines. Additionally, the Admiral Club lounges are located between Gates H6 and K6, Gate L1, and near Gate G8. Terminal 5 has some lounges in it.

  • Are there any hotels near Oakland International Airport (OAK)?

    The SpringHill Suites by Marriott Oakland Airport is among the most convenient hotels where you can book a room in the case of late arrival at the airport. It is located 1.7 miles away and has facilities such as an indoor spa.

  • Are there Pet Relief Areas in O'Hare International Airport (ORD)?

    There are several Pet Relief Areas in O'Hare International Airport (ORD). An area inside Terminal 1's lower level is accessible by taking the elevator to the lower level and proceeding to the Baggage Claim, exit through Door 1A, and you will have the area on your left. Terminal 2's location is accessible by taking the elevator to the lower level, exiting through Door 2E, and the site will also be on your left. Terminal 3 is located inside the Main Hall of the airport next to the Lotto booth found near Gate K1.

  • What flights are available from O’Hare International Airport (ORD) to Oakland International Airport (OAK)?

    There are both direct and connecting flights between the destinations. Spirit Airlines is the only airline that offers direct flights between the destinations. However, they also have flights with a layover at Harry Reid International Airport (LAS). Delta Airlines also makes flights with a layover at Salt Lake City International Airport (SLC).

  • Which airlines offer extra legroom and free seat selection on Chicago to Oakland flights?

    Among airlines operating Chicago to Oakland flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago to Oakland?

    Only Southwest operates flights between Chicago and Oakland.

  • Which airports can I use when flying from Chicago to Oakland?

    Flights from Chicago to Oakland may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Oakland (OAK).

  • Which airlines include bags at no extra cost on Chicago to Oakland flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago to Oakland?

    Only Economy Class is available on flights from Chicago to Oakland.

  • How much can I save by taking a layover when flying from Chicago to Oakland?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $334 round-trip via San Diego (SAN), compared to $393 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to Oakland?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago to Oakland pass through?

    One-stop flights from Chicago to Oakland most commonly connect through:

    • Salt Lake City (SLC) - 25% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 20% of one-stop connections
    • San Diego (SAN) - 19% of one-stop connections
    • Seattle/Tacoma Intl (SEA) - 16% of one-stop connections

    Salt Lake City (SLC) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago to Oakland?

    On the Chicago to Oakland route, being flexible with your departure day can save you up to 32%. Saturday is the cheapest day at $349 round-trip on average, while Sunday is the most expensive at $507: a $158 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • At what point is a flight considered delayed from Chicago to Oakland?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Oakland route, 32% of flights were delayed in the past 3 months, with delays averaging 2 hours 10 minutes.

  • How are flight departures from Chicago to Oakland spread across the day?

    Morning is the busiest departure period on Chicago to Oakland flights, with 50% of flights leaving in that window. Evening departures account for 50%, afternoon flights for 0%, and night flights for 0%.

  • What popular places can I visit in Oakland?

    Some of the most popular sights in Oakland are Oakland Arena, Fox Theater and Jack London Square. These are among the most viewed places in Oakland on KAYAK.

  • What are the earliest and latest flights from Chicago to Oakland?

    These are the earliest and latest flight times available from Chicago to Oakland:

    • Earliest: departs at 9:35 am and lands at 2:13 pm
    • Latest: departs at 11:05 pm and lands at 3:43 am.

    The flight takes about 4h 38m.

  • How long is a flight from Chicago to Oakland?

    A nonstop flight from Chicago to Oakland takes 4h 38m, covering 1,845 miles.

  • Do I need a passport to fly from Chicago to Oakland?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Chicago to Oakland changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $228 to $1,749. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago to Oakland looking right now?

    One-way fares from Chicago to Oakland are currently lower than usual. Average one-way flight prices are about $132, which is 55% below the typical average for this route.

  • How does Southwest’s on-time performance compare to other airlines on Chicago to Oakland flights?

    Southwest is the only airline operating Chicago to Oakland flights. 68% of its flights are on time.

  • How do delay rates compare for morning and evening flights from Chicago to Oakland?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago to Oakland?

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 18m, compared with 6h 26m via Phoenix Sky Harbor Intl (PHX) and 6h 26m via Kansas City (MCI).

  • What is the time difference between Chicago and Oakland?

    Oakland is 2 hours behind Chicago (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Oakland Airport (OAK)?

    Oakland Airport (OAK) hosts 5 major car rental companies, with daily rates starting from around $21 for economy cars. Top options include:
    · Dollar
    · Thrifty
    · Budget
    · Hertz
    · Alamo

  • How much should I expect to pay for a Chicago to Oakland flight?

    Round-trip flights from Chicago to Oakland range from $303 to $530, with an average of $400 over the past 12 months. Anything below $303 counts as a good deal.

Your guide to booking Chicago to Oakland flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Sunday. On this route, Saturday flights average $349 - about $158 less than Sunday (31% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago to Oakland trip for April. Fares historically average $310 round-trip in that month - typically $208 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through San Diego Airport (SAN) can be cheaper than flying direct. The cheapest layover option averages $334 round-trip on this route - about $59 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Oakland Airport.
    - Oakland Airport Executive Hotel
    - Holiday Inn Express & Suites Oakland-Airport By IHG
    - Holiday Inn & Suites Oakland - Airport By IHG
  • Two international airports serve the city of Chicago. Although the O'Hare International Airport (ORD) is the central hub for flights around the city, the Midway International Airport (MDW) is closer to downtown Chicago of the two airports. They are located 18 miles and 12.5 miles away from the city center.
  • The BART train is the best way to get from the Oakland International Airport (OAK) to downtown Oakland. It costs around $6 for a ticket, and you can catch it at the station located at the Coliseum. It will take you 10min to complete the journey.
  • Travelers to Oakland can rely on three airports for their transportation needs: Norman Y. Mineta International Airport, Oakland International Airport (OAK), and Reid Hillview Airport. The former Oakland International (OAK) is the most convenient option for traveling to the city since it's 6 miles distance from the center of Oakland.
  • The most convenient way to move from downtown to O'Hare International Airport (ORD) is via the Blue Line, which only takes 45min to complete the journey and around $5 as a fare.
  • On the curbside of Terminal 2, you will find wheelchairs in the Oakland International Airport (OAK). If you have mobility challenges, it would be better to use the services offered in Terminal 2. It would also be better to contact your airlines before traveling for arranged assistance.

Prefer to fly direct from Chicago to Oakland?

 
Find which airlines fly direct from Chicago to Oakland Airport, which days they fly and book direct flights.

Direct departures

Chicago to Oakland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Oakland to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

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Everything you need to know for your flight from Chicago to Oakland

Information on your arrival and departure airports