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MDW to OAK

Chicago to Oakland Flights

Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.

Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fare₹15,850Delta Air Lines
Fastest8h 10mgate to gate
Options found15flights on this route
Find your flight MDW OAK

Available Flights & Fares

Compare fares, timings and baggage. Pick the flight that suits your trip.

Prices in INR
15 flight options

Fares are checked again before payment.

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Delta Air Lines
Delta Air Lines
DL-1063
10:59
2026-10-30
Chicago (MDW)Midway
14H :57 M
2 Stops
ATL · 3h 59m Atlanta (ATL), United States
SLC · 2h 57m Salt Lake City (SLC), United States
23:56
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-2417
12:49
2026-10-30
Chicago (MDW)Midway
13H :07 M
2 Stops
ATL · 2h 17m Atlanta (ATL), United States
SLC · 2h 57m Salt Lake City (SLC), United States
23:56
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-2417
12:49
2026-10-30
Chicago (MDW)Midway
35H :09 M
2 Stops
ATL · 23h 40m Atlanta (ATL), United States
SLC · 3h 40m Salt Lake City (SLC), United States
21:58
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-5373
09:29
2026-10-30
Chicago (MDW)Midway
28H :32 M
2 Stops
DTW · 20h 32m Detroit (DTW), United States
SLC · 0h 41m Salt Lake City (SLC), United States
12:01
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-1063
10:59
2026-10-30
Chicago (MDW)Midway
27H :02 M
2 Stops
ATL · 18h 12m Atlanta (ATL), United States
SLC · 0h 42m Salt Lake City (SLC), United States
12:01
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-1063
10:59
2026-10-30
Chicago (MDW)Midway
31H :23 M
2 Stops
ATL · 21h 47m Atlanta (ATL), United States
SLC · 1h 34m Salt Lake City (SLC), United States
16:22
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-2417
12:49
2026-10-30
Chicago (MDW)Midway
25H :12 M
2 Stops
ATL · 16h 30m Atlanta (ATL), United States
SLC · 0h 42m Salt Lake City (SLC), United States
12:01
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-2417
12:49
2026-10-30
Chicago (MDW)Midway
29H :33 M
2 Stops
ATL · 20h 05m Atlanta (ATL), United States
SLC · 1h 34m Salt Lake City (SLC), United States
16:22
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-4688
13:27
2026-10-30
Chicago (MDW)Midway
24H :34 M
2 Stops
DTW · 16h 33m Detroit (DTW), United States
SLC · 0h 41m Salt Lake City (SLC), United States
12:01
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-4677
18:44
2026-10-30
Chicago (MDW)Midway
19H :17 M
2 Stops
DTW · 11h 17m Detroit (DTW), United States
SLC · 0h 41m Salt Lake City (SLC), United States
12:01
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-4677
18:44
2026-10-30
Chicago (MDW)Midway
29H :14 M
2 Stops
DTW · 20h 47m Detroit (DTW), United States
SLC · 1h 19m Salt Lake City (SLC), United States
21:58
2026-10-31
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-5373
09:29
2026-10-30
Chicago (MDW)Midway
16H :27 M
2 Stops
DTW · 8h 35m Detroit (DTW), United States
SLC · 0h 41m Salt Lake City (SLC), United States
23:56
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-4688
13:27
2026-10-30
Chicago (MDW)Midway
12H :29 M
2 Stops
DTW · 4h 36m Detroit (DTW), United States
SLC · 0h 41m Salt Lake City (SLC), United States
23:56
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-5373
09:29
2026-10-30
Chicago (MDW)Midway
8H :53 M
2 Stops
DTW · 0h 32m Detroit (DTW), United States
SLC · 1h 13m Salt Lake City (SLC), United States
16:22
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-5469
10:12
2026-10-30
Chicago (MDW)Midway
8H :10 M
2 Stops
MSP · 0h 37m Minneapolis (MSP), United States
SLC · 0h 53m Salt Lake City (SLC), United States
16:22
2026-10-30
Oakland (OAK)Metropolitan Oak Intl
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces

Recommended hotels in Oakland

Stay options near the arrival city for the same travel date.

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Airfare Highlights

From flights departing on Fri, 30 Oct 2026.

Lowest fare ₹15,850 Delta Air Lines 10:59
Earliest departure ₹26,033 Delta Air Lines 09:29
Shortest duration ₹83,715 Delta Air Lines 10:12
Night 00:00-05:59 No option Open full search for more
Morning 06:00-11:59 ₹15,850 Delta Air Lines at 10:59
Afternoon 12:00-17:59 ₹15,850 Delta Air Lines at 12:49
Evening 18:00-23:59 ₹26,033 Delta Air Lines at 18:44

Departure & Arrival Airport Details

Chicago (MDW)

Midway

United States

GMT -6

Latitude: 41.785999

Longitude: -87.752403

Oakland (OAK)

Metropolitan Oak Intl

United States

GMT -8

Latitude: 37.721298

Longitude: -122.221001

Distance: Chicago (MDW), United States to Oakland (OAK), United States - 2,960.86 km
Flights shown for 30 Oct 2026. View all flights opens the complete search result.
Route forecast

Weather in Chicago and Oakland

Live forecast for both cities, 12 Oct to 15 Oct.

Departure city

Chicago

Thu, 15 Oct
23°CClear skyLow 14°
90% humidity 11 km/h wind
  • Mon20° / 15°
  • Tue24° / 14°
  • Wed23° / 17°
Arrival city

Oakland

Thu, 15 Oct
18°CPartly cloudyLow 12°
78% humidity 2 km/h wind
  • Mon18° / 13°
  • Tue18° / 13°
  • Wed17° / 11°

Forecast data from MET Norway, CC BY 4.0.

Smart travel dates

Holidays and peak dates for Oakland

Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.

Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).

  • 12OctColumbus DayMonday
  • 12OctColumbus DayMonday
  • 12OctIndigenous Peoples' DayMonday
  • 11NovVeterans DayWednesday
  • 26NovThanksgiving DayThursday
  • 25DecChristmas DayFriday

Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here, so check the exact date for your travel year.

Compare your journey

How to travel Chicago to Oakland

Ways to make this trip that you can book on FlyX, compared by price and journey time.

OptionFromJourney timeAvailabilityAction
Connecting flight₹15,850Longer, includes a stop15 options

Air distance is about 2,961 km.

Road distance and coach duration are approximate estimates from the air distance, not a timetable.

Airlines flying from Chicago to Oakland

Compare fares, stops, baggage and refundability across the airlines flying this route.

Delta Air Lines Flights

from ₹15,85015 flights
Fares from
₹15,850
Non-stop
None in these results
Departures
15 in the list above

Route Overview & Flight Facts

Fastest flight duration8h 10m · Delta Air Lines
First departure of the day09:29 · Delta Air Lines
Last departure of the day18:44 · Delta Air Lines
Flight options found15
Airport codesChicago–MDW, Oakland–OAK

Fares and timings are indicative. The exact price is confirmed with the airline when you search.

Flight Schedule, Timings & Airfare Insights

Daily Flight Schedule & Travel Duration

The search for Fri, 30 Oct found 15 flight options. The first flight leaves around 09:29 and the last around 18:44. The fastest flight takes about 8h 10m.

Morning vs Evening Departure Fares

Lowest fare by departure window: Morning from ₹15,850, Afternoon from ₹15,850, Evening from ₹26,033. These observations do not predict the cheapest departure window on other dates.

Cheapest Airfare & Best Time to Book

Search your travel dates to compare current fares. Prices change with airline seat availability.

One-Way vs Round-Trip Fare Comparison

Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.

Online Web Check-In & Boarding Pass

Check the operating airline’s opening time and check-in deadline for each sector. Seat charges and availability depend on your fare. Use the airline reference and the links on Web Check-in.

How to Book Cheap Flights on FlyX

  1. 1
    Enter your travel details

    Choose one-way or round-trip, pick your dates and travellers in the search form above.

  2. 2
    Compare search results

    Sort or filter the Chicago–Oakland results by price, departure time, stops and airline.

  3. 3
    Open the fare choices

    Check baggage allowance and refundability for each fare type before continuing.

  4. 4
    Review the final price

    Review the refreshed supplier fare, coupon saving and selected payment-method fee before you pay.

  5. 5
    Pay securely

    UPI, cards, net banking and wallets supported; payment and ticket issuance have separate statuses. If issuance is pending, follow the booking status; the confirmed ticket is sent after issuance.

Why Book Your Flight with FlyX?

Compare the available Chicago to Oakland options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.

Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.

Fare checked before paymentCoupon eligibility checkedBooking status trackingBooking support

Exclusive Flight Offers & Promo Coupons

Coupon codeOfferMax saving
FLYX20Up to 20% Off on Flights₹1,500

Check coupon eligibility and the final discount on the review page before you pay. View full terms.

Frequently Asked Questions

Is it worth booking Chicago to Oakland flights in advance?

There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. On the Chicago to Oakland dates shown on this page, the lowest fare is on a Friday at ₹15,850. This can change from week to week.

How far is Chicago from Oakland by air?

The direct air distance between Chicago (MDW) and Oakland (OAK) is about 2,961 km. Actual flight time varies with the routing the airline files and with winds on the day.

Are there non-stop flights from MDW to OAK?

Not on the dates shown here. Every Chicago to Oakland option on this page has at least one stop. Non-stop service can differ by season and by day, so check nearby dates before you decide.

Which airlines fly Chicago to Oakland?

Delta Air Lines is listed on this route for the dates shown here. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.

How long is the flight from Chicago to Oakland?

Every option on this page has at least one stop, and the shortest total journey time is about 8h 10m including the layover. Non-stop service on this route can vary by season and by day.

What is the cheapest Chicago to Oakland flight fare?

The lowest Chicago to Oakland fare on this page is ₹15,850. Fares on the same dates run up to ₹83,715, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.

What time do Chicago to Oakland flights depart?

On the dates shown here, the first departure is around 09:29 and the last around 18:44, local time at Chicago. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.

Why does the price change after clicking Book Now?

Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay. If it has moved, you see the new figure before any payment.

Before you book this route

Check the airport codes MDW–OAK, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.

Where these fares come from

The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price. Run a search to see what is available for your own dates.

Fares shown are for departures on .

Check official travel requirements

Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.

For payment, ticket issuance or a change request, see FlyX support. About FlyX.

United States travel guide for Indian travellers

Planning more than the flight? Our United States guide covers the visa process for Indian passport holders, best time to go, how long to plan for, and which places are worth the days you have. Long-haul city breaks and national parks.

Read the United States travel guide

What to Expect When Booking Your Flight

The MDW to OAK cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.

Approx route distance: 2,960.86 km.

Before you book

Compare nearby dates

The date strip opens the complete search result for the route and selected date.

Use filters

Shortlist by price, stops, departure time and refundable fare preference.

Check fare choices

Continue to Booking opens the verified fare choices, including baggage and refundability, before review.

Lowest Chicago to Oakland airfare, in 30 days and in 90 days

Cheapest FareFareDateAirlineDeparture
Lowest Airfare ₹15,850 30/10/2026 Delta Air Lines 10:59
Cheapest Airfare Within 30 Days ₹15,533 07/11/2026 Delta Air Lines 10:59
Cheapest Airfare Within 90 Days ₹15,058 06/01/2027 Delta Air Lines 10:59

Book Chicago to Oakland Flight Tickets on FlyX

FlyX lists each Chicago to Oakland flight in these results with its fare, departure time, stops, layover airport and baggage, so you can compare air tickets side by side. To find a cheap ticket, sort by price and check what baggage the fare includes. The fare is checked with the airline again before you pay.

Chicago to Oakland Flight Distance, Duration and Time

The aerial distance between Chicago and Oakland is about 2,961 KM. In these results, journey times range from 8h 10m to 35h 9m. Flights with a layover take longer because the total includes the connection time.

Chicago to Oakland Flight Schedule and Timing

The search for these dates returned 15 flight options. The first departure from Chicago is at 09:29 and the last is at 18:44. Flights leave from Midway and land at Metropolitan Oak Intl.

Flight Route Details & Analysis

Flight DetailsInformation
RouteChicago to Oakland
Aerial Distance2,961 KM
Flight Duration8h 10m - 35h 9m
Airport CodesChicago - MDW, Oakland - OAK
Total Flights Available15 flights0 direct15 with layovers
First Flight DepartureDeparts at 09:29
Last Flight DepartureDeparts at 18:44
Early Morning Flights (12 AM - 8 AM)No flights in this time slot
Morning Flights (8 AM - 12 PM)7 flights0 direct7 with layovers
Afternoon Flights (12 PM - 4 PM)6 flights0 direct6 with layovers
Evening Flights (4 PM - 8 PM)2 flights0 direct2 with layovers
Night Flights (8 PM - 12 AM)No flights in this time slot

Airport Information & Terminals

MDW: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.

OAK: Oakland airport. Oakland airport transfer should be matched to the exact hotel, suburb or meeting area. Rail can work well for light luggage, but late arrivals, winter weather and family baggage often make a direct cab or booked transfer easier.

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