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Latest Flight Deals from Chicago to Oakland

Book one-way or return flights from Chicago to Oakland from as little as AU$ 98. Choose from the popular airlines below and book your flight today!

  • One way
  • Return
      • ORD22:52
        14h 20m
        1 stop
        OAK11:12
        Tue, May 21|Chicago - Oakland|Spirit Airlines
        AU$ 98AU$ 195
        50% OFF
        50% OFF
        AU$ 195AU$ 98
      • MDW22:59
        14h 13m
        1 stop
        OAK11:12
        Tue, May 7|Chicago - Oakland|Frontier Airlines
        AU$ 116AU$ 195
        40% OFF
        40% OFF
        AU$ 195AU$ 116
      • ORD22:57
        11h 55m
        1 stop
        OAK08:52
        Tue, May 14|Chicago - Oakland|Spirit Airlines
        AU$ 120AU$ 195
        39% OFF
        39% OFF
        AU$ 195AU$ 120
      • MDW21:10
        16h 2m
        1 stop
        OAK11:12
        Tue, May 21|Chicago - Oakland|Frontier Airlines
        AU$ 122
        AU$ 122
      • MDW22:59
        25h 18m
        1 stop
        OAK22:17
        Fri, Apr 26|Chicago - Oakland|Frontier Airlines
        AU$ 129
        AU$ 129
      • ORD09:27
        11h 2m
        1 stop
        OAK18:29
        Tue, May 7|Chicago - Oakland|Spirit Airlines
        AU$ 142
        AU$ 142
      • ORD16:05
        8h 50m
        1 stop
        OAK22:55
        Sat, May 25|Chicago - Oakland|Spirit Airlines
        AU$ 145
        AU$ 145
      • ORD22:52
        14h 12m
        1 stop
        OAK11:04
        Tue, Jun 4|Chicago - Oakland|Spirit Airlines
        AU$ 148
        AU$ 148
      • ORD19:52
        6h 23m
        1 stop
        OAK00:15
        Mon, Apr 29|Chicago - Oakland|Spirit Airlines
        AU$ 148
        AU$ 148
      • ORD09:27
        11h 2m
        1 stop
        OAK18:29
        Tue, Apr 30|Chicago - Oakland|Spirit Airlines
        AU$ 148
        AU$ 148
      • CHI13:00
        3h 5m
        Direct
        OAK14:00
        Fri, May 3|Chicago - Oakland|Spirit Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to Oakland? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Oakland. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to Oakland

View airlines operating flights from Chicago to Oakland. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From AU$ 91
Frontier Airlines
From AU$ 116
Alaska Airlines
From AU$ 167
Delta Air Lines
From AU$ 172
Sun Country Airlines
From AU$ 181
Southwest Airlines
From AU$ 225
American Airlines
From AU$ 239
United Airlines
From AU$ 255
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Oakland

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Oakland.

  • Cheapest
    Spirit Airlines
    ORD
    07:03
    18h 3m
    2 transfer
    OAK
    23:06
    O'Hare International Airport - Oakland International Airport
    Tue, May 7Spirit Airlines
    AU$ 91
  • Frontier Airlines
    MDW
    22:59
    14h 13m
    1 transfer
    OAK
    11:12
    Midway International Airport - Oakland International Airport
    Tue, May 7Frontier Airlines
    AU$ 116
  • Frontier Airlines
    MDW
    22:59
    14h 13m
    1 transfer
    OAK
    11:12
    Midway International Airport - Oakland International Airport
    Tue, May 7Frontier Airlines
    AU$ 116
    Find More Flights

How do I find the cheapest flights?

  • When are flight from Chicago (CHI) to Oakland (OAK) the cheapest?

    Airlines adjust prices for flights from Chicago to Oakland based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Chicago (CHI) to Oakland (OAK) cost?

    According to Trip.com's data, the lowest price is around AU$ 614.

  • How long is the flights from Chicago (CHI) to Oakland (OAK)?

    It takes about 5 hours 58 minutes to fly from Chicago (CHI) to Oakland (OAK).

  • What is the transportation method from the main airport to downtown in Oakland?

    • The distance from Oakland International Airport to downtown is about 11km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Chicago (CHI) to Oakland (OAK)?

    Airlines with flights from Chicago (CHI) to Oakland (OAK): Southwest Airlines.

  • What's the most popular airline for direct flights from Chicago (CHI) to Oakland (OAK)?

    Southwest Airlines operates 5 direct flights from Chicago (CHI) to Oakland (OAK).

  • How many airports in Oakland (OAK)?

    There are 1 airport(s) in Oakland (OAK): Oakland International Airport.

How to find a cheap flight from Chicago to Oakland

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Oakland. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information from Chicago to Oakland

Cheapest direct flight price

AU$ 98

Cheapest return ticket price

AU$ 505

Off-season for travel

December

Peak season for travel

October

Flight distance

2,969.56km

Average flight time

5 hours 58 minutes

Popular airline

Alaska Airlines

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