OAK - CHI

$79 Find Cheap Flights from Oakland to Chicago - 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 Oakland to Chicago departing on 9/10. 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
$158
Typical prices: $359-$582
Frontier
Mon 9/14Mon 9/21
OAK - ORD • 1 stop
Cheapest non-stop
$237
Typical prices: $322-$890
Southwest
Mon 9/14Wed 9/23
OAK - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 02m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $233 (round-trip)
Shortest trip • 5h 55m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 22% price drop
Most popular
Good to know
Good to know
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Flight Deals

Cheap Flights from Oakland to Chicago (OAK-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Chicago 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 Oakland to Chicago

Mon, Sep 14 - Mon, Sep 21
Frontier Logo
10:17 am - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
17h 21m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
$158Frontier
Wed, Sep 30 - Mon, Oct 5
Frontier Logo
12:47 pm - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
14h 51m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
$158Frontier
Thu, Sep 17 - Mon, Sep 21
Frontier Logo
10:17 am - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
17h 21m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
16h 56m1 stop Las Vegas Harry Reid Intl
$158Frontier
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
9:30 pm - 5:40 amOAK  Oakland-MDW Chicago Midway
6h 10m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:55 pm - 12:35 amMDW  Chicago Midway-OAK Oakland
4h 40mnonstop
$229Southwest
Mon, Sep 21 - Sat, Sep 26
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
1:50 pm - 5:55 pmMDW  Chicago Midway-OAK Oakland
6h 05m1 stop Long Beach Municipal
$229Southwest
Mon, Sep 21 - Sat, Sep 26
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
11:00 am - 5:45 pmMDW  Chicago Midway-OAK Oakland
8h 45m2 stops Kansas City Seattle/Tacoma Intl
$234Southwest
Wed, Sep 30 - Mon, Oct 5
Delta Logo
12:39 pm - 9:55 pmOAK  Oakland-ORD Chicago O'Hare Intl
7h 16m1 stop Salt Lake City
Delta Logo
7:40 pm - 11:59 pmORD  Chicago O'Hare Intl-OAK Oakland
6h 19m1 stop Salt Lake City
$239Delta
Wed, Sep 30 - Tue, Oct 6
Delta Logo
12:39 pm - 9:55 pmOAK  Oakland-ORD Chicago O'Hare Intl
7h 16m1 stop Salt Lake City
Delta Logo
7:15 pm - 11:56 pmORD  Chicago O'Hare Intl-OAK Oakland
6h 41m1 stop Salt Lake City
$239Delta
Tue, Oct 20 - Tue, Oct 27
Alaska Airlines Logo
9:59 am - 6:53 pmOAK  Oakland-ORD Chicago O'Hare Intl
6h 54m1 stop San Diego
Alaska Airlines Logo
2:21 pm - 11:42 pmORD  Chicago O'Hare Intl-OAK Oakland
11h 21m1 stop San Diego
$277Alaska Airlines
Mon, Sep 28 - Tue, Sep 29
Alaska Airlines Logo
1:29 pm - 11:59 pmOAK  Oakland-ORD Chicago O'Hare Intl
8h 30m1 stop San Diego
Alaska Airlines Logo
2:18 pm - 9:28 pmORD  Chicago O'Hare Intl-OAK Oakland
9h 10m1 stop San Diego
$277Alaska Airlines
Booking Insights

KAYAK's insights & trends for Oakland to Chicago flights

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Oakland, California to Chicago departing in September.

Flight prices are below average for this route right now.

Flights to Chicago from Oakland, California usually cost between $364 and $587 in September.
The lowest price found in the past 5 days was $158 on Frontier (Sep 16-Sep 21).

What is the cheapest Oakland to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Oakland to Chicago costs $278 on the route between Oakland (OAK) and Chicago Midway Airport (MDW). It is also the most popular route.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Chicago, 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 Oakland to Chicago is February, where tickets cost $364 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $544 and $542 respectively.

Can I save money by flying with a layover from Oakland to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $393 on average.

Expert advice

Expert advice for your flight from Oakland to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

Good to know

Low season

February

Cheapest flight

$79
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Oakland to Chicago O'Hare Airport

When to book flights from Oakland to Chicago

Are your dates flexible? Find out the best times to travel from Oakland to Chicago 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 flights from Oakland to Chicago

  • Are there nursing rooms at MDW?

    MDW has a nursing room in Concourse C, next to the yoga room. This room, well-furnished with comfy seats, features a hand washing station and clean utensils. If you're a breastfeeding mother, you can use this nursing room to breastfeed and change your infant privately before continuing your journey.

  • Does OAK have any fun places I can visit?

    While waiting for your flight to Chicago at OAK, you should check out the airport's public art displays in Terminal 2, near the baggage claim area, and in Terminal 1, on the Airside. Additionally, there are a variety of retail shops throughout both terminals you can check out.

  • Which Chicago Airport has an on-site hotel?

    If you'd like to land at a Chicago airport with an on-site hotel, you should book a flight that lands at ORD, as this public transit hub is home to two on-site hotels, Hilton Chicago O'Hare Airport Hotel and Aloft Chicago O'Hare. Hilton Chicago O'Hare Airport Hotel is located opposite Terminal 2. It is connected to all the airport terminals via an underground Walkway. Aloft Chicago O'Hare is located between Terminals 1, 2, and 3. Since both hotels feature great amenities, staying at either would be a move you'll not regret.

  • Does OAK have any lounges?

    Oakland International Airport has a lounge in Terminal 1, on the Airside, near Gates 8 and 8A. This relaxing space, referred to as the Escape lounge, is open to all economy travelers at the airport. If you're one, you can access it if you're open to purchasing a day pass, annual membership, or pay at the door.

  • What is the cheapest flight from Oakland to Chicago?

    In the last 5 days, the lowest price for a flight from Oakland to Chicago was $79 for a one-way ticket and $158 for a round-trip.

  • Do I need a passport to fly between Oakland and Chicago?

    No, a passport isn't needed to fly from Oakland to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Oakland to Chicago?

    Oakland is served by only 1 airport and there are 2 airports in Chicago. You will leave Oakland from Oakland and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Oakland to Chicago?

    American Airlines, JetBlue, Alaska Airlines, Delta, and Air Canada offer inflight Wi-Fi service on the Oakland to Chicago flight route.

  • Which aircraft models fly most regularly from Oakland to Chicago?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Oakland to Chicago flight route.

  • Which airline alliances offer flights from Oakland to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Oakland and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Oakland to Chicago?

    There are nonstop flights from Oakland to Chicago on a daily basis.

  • Which is the best airline for flights from Oakland to Chicago, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Oakland to Chicago are Southwest and Alaska Airlines. With an average price for the route of $429 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $354 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Oakland to Chicago?

    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 Oakland to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Oakland 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 Oakland to Chicago?

    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 with an airline and back to Oakland with another airline.

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

    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 from Oakland 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 Oakland to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $208 or less one-way and $366 or less round-trip.
  • In Oakland, you can board your plane to Chicago at Norman Y. Mineta San Jose International Airport (SJC), Oakland International Airport (OAK), or San Francisco International Airport (SFO). Among the three airports, OAK has the smallest crowds. It is also the nearest to Oakland. Given its proximity to Oakland and its small passenger crowds, OAK is the most convenient Oakland airport to fly out to Chicago.
  • You can travel to OAK from downtown Oakland through three public means of transit. They include the subway, bus, and taxi. The means you choose will be determined by how fast you'd like to travel and how much you are willing to spend as fare. If you'd like to travel cheaply, you should travel by subway or bus. However, if you'd like to travel quickly, you should travel by taxi.
  • If you drive to OAK, you can count on easily finding a spot you can leave your car in for the entire duration of your trip, as OAK is home to four on-airport parking options that offer long-term parking services. Premium, Hourly, Daily, and Economy are located in different parts of the airport. Premium is the closest of the four, as it is situated adjacent to the terminals.
  • In Chicago, you can land at either O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). ORD usually has more passenger traffic than MDW. Hence, it normally has long queues. This being the case, to avoid long queues once you land, you should book a flight from Chicago that lands at MDW.
  • Once you land at ORD or MDW, there are several towns you can get to easily, other than Chicago. They include Elmhurst, Aurora, Gurnee, Dundee, New Buffalo, and Lake Geneva.

Prefer to fly direct from Oakland to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Oakland to Chicago.
Find which airlines fly direct from Oakland Airport to Chicago, which days they fly and book direct flights.

Direct departures

Oakland to Chicago

Monday

Southwest

Southwest

Tuesday

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Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

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See more direct flights

Direct returns

Chicago to Oakland

Monday

Southwest

Southwest

Tuesday

Southwest

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

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

Information on your arrival and departure airports