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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 US$90. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • ORD17:59
        7h 53m
        1 stop
        OAK23:52
        Thu, Aug 22|Chicago - Oakland|Alaska Airlines
        US$90US$114
        21% OFF
        21% OFF
        US$114US$90
      • ORD17:50
        8h 5m
        1 stop
        OAK23:55
        Fri, Aug 16|Chicago - Oakland|Alaska Airlines
        US$91US$114
        20% OFF
        20% OFF
        US$114US$91
      • ORD06:00
        19h 52m
        1 stop
        OAK23:52
        Tue, Aug 27|Chicago - Oakland|Alaska Airlines
        US$91US$114
        20% OFF
        20% OFF
        US$114US$91
      • ORD22:17
        12h 14m
        1 stop
        OAK08:31
        Mon, Jul 1|Chicago - Oakland|Spirit Airlines
        US$91
        US$91
      • ORD17:50
        8h 5m
        1 stop
        OAK23:55
        Mon, Aug 19|Chicago - Oakland|Alaska Airlines
        US$92
        US$92
      • ORD17:59
        7h 53m
        1 stop
        OAK23:52
        Mon, Sep 16|Chicago - Oakland|Alaska Airlines
        US$93
        US$93
      • ORD17:59
        7h 53m
        1 stop
        OAK23:52
        Sat, Sep 21|Chicago - Oakland|Alaska Airlines
        US$93
        US$93
      • ORD22:38
        11h 59m
        1 stop
        OAK08:37
        Mon, Jul 15|Chicago - Oakland|Spirit Airlines
        US$94
        US$94
      • ORD22:38
        11h 59m
        1 stop
        OAK08:37
        Mon, Aug 12|Chicago - Oakland|Spirit Airlines
        US$94
        US$94
      • ORD17:59
        7h 53m
        1 stop
        OAK23:52
        Mon, Aug 26|Chicago - Oakland|Alaska Airlines
        US$94
        US$94
      • CHI13:00
        3h 5m
        Direct
        OAK14:00
        Mon, Jul 8|Chicago - Oakland|Alaska 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.

Alaska Airlines
From US$90
Spirit Airlines
From US$91
Sun Country Airlines
From US$102
Delta Air Lines
From US$114
Frontier Airlines
From US$116
United Airlines
From US$141
American Airlines
From US$147
Southwest Airlines
From US$152
Allegiant Air
From US$235
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
    Alaska Airlines
    ORD
    17:59
    7h 53m
    1 transfer
    OAK
    23:52
    O'Hare International Airport - Oakland International Airport
    Thu, Aug 22Alaska Airlines
    US$90
  • Frontier Airlines
    MDW
    19:55
    14h 15m
    1 transfer
    OAK
    08:10
    Midway International Airport - Oakland International Airport
    Tue, Jul 9Frontier Airlines
    US$116
  • Allegiant Air
    RFD
    21:33
    27h 30m
    1 transfer
    OAK
    23:03
    Chicago Rockford International Airport - Oakland International Airport
    Sun, Jul 7Allegiant Air
    US$235
  • Allegiant Air
    RFD
    21:33
    27h 30m
    1 transfer
    OAK
    23:03
    Chicago Rockford International Airport - Oakland International Airport
    Sun, Jul 7Allegiant Air
    US$235
    Find More Flights

How do I find the cheapest flights?

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

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

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

    According to Trip.com's data, the lowest price is around $423.

  • How long does it take to fly from Chicago (CHI) to Oakland (OAK) and what is the distance?

    It takes around 5 hours 40 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. It takes about 30 minutes by taxi.

  • 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 and United Airlines.

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 nonstop flight price

$89

Cheapest round-trip ticket price

$302

Off-season for travel

May

Peak season for travel

September

Flight distance

2,969.56km

Average flight time

5 hours 40 minutes

Popular airline

American Airlines

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