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OAKMDWSat, 14 Nov
Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fare₹12,322Delta Air Lines
Fastest4h 20mgate to gate
Options found52flights on this route
Find your flightOAK → MDW
Available Flights & Fares
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Delta Air Lines
DL-4061
05:55
2026-11-14
Oakland (OAK)Metropolitan Oak Intl
8H :44 M
2 Stops
SLC
· 1h 11m Salt Lake City (SLC), United States
MSP
· 1h 24m Minneapolis (MSP), United States
16:39
2026-11-14
Chicago (MDW)Midway
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
₹12,322
Flight DetailsOAK to MDW - 8H :44 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Delta Air Lines
DL-4061
05:55
2026-11-14
Oakland (OAK)Metropolitan Oak Intl
10H :09 M
2 Stops
SLC
· 1h 00m Salt Lake City (SLC), United States
DTW
· 2h 20m Detroit (DTW), United States
18:04
2026-11-14
Chicago (MDW)Midway
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
₹15,627
Flight DetailsOAK to MDW - 10H :09 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Fare RulesRefundable fare. Final rules are verified before booking.
Delta Air Lines
DL-4061
05:55
2026-11-14
Oakland (OAK)Metropolitan Oak Intl
25H :51 M
2 Stops
SLC
· 1h 00m Salt Lake City (SLC), United States
DTW
· 17h 50m Detroit (DTW), United States
09:46
2026-11-15
Chicago (MDW)Midway
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
₹26,655
Flight DetailsOAK to MDW - 25H :51 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
No flights match the selected filters. Clear filters or open full search.
Airfare Highlights
From flights departing on Sat, 14 Nov 2026.
Lowest fare₹12,322Delta Air Lines05:55
Earliest departure₹36,220American Airlines05:00
Shortest duration₹16,956American Airlines23:39
Night
00:00-05:59
₹12,322Delta Air Lines at 05:55Morning
06:00-11:59
₹16,956American Airlines at 06:01Afternoon
12:00-17:59
₹16,956American Airlines at 13:42Evening
18:00-23:59
₹16,956American Airlines at 23:39
Departure & Arrival Airport Details
Oakland (OAK)
Metropolitan Oak Intl
United States
GMT -8
Latitude: 37.721298
Longitude: -122.221001
Chicago (MDW)
Midway
United States
GMT -6
Latitude: 41.785999
Longitude: -87.752403
Distance: Oakland (OAK), United States to Chicago (MDW), United States - 2,960.86 km
Flights shown for 14 Nov 2026. View all flights opens the complete search result.
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).
11NovVeterans DayWednesdayPeak
26NovThanksgiving DayThursdayPeak
25DecChristmas DayFridayPeak
01JanNew Year's DayFridayPeak
18JanMartin Luther King, Jr. DayMondayPeak
12FebLincoln's BirthdayFridayPeak
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 Oakland to Chicago
Ways to make this trip that you can book on FlyX, compared by price and journey time.
OptionFromJourney timeAvailabilityAction
Non-stop flight Fastest₹16,9564h 20m7 flights
Connecting flight₹12,322Longer, includes a stop45 options
Air distance is about 2,961 km. 2 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from Oakland to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
AM
American Airlines Flights
from ₹16,95636 flights
Fares from
₹16,956
Non-stop
7 in these results
Departures
36 in the list above
DE
Delta Air Lines Flights
from ₹12,32216 flights
Fares from
₹12,322
Non-stop
None in these results
Departures
16 in the list above
Route Overview & Flight Facts
Fastest flight duration
4h 20m · American Airlines
First departure of the day
05:00 · American Airlines
Last departure of the day
23:39 · American Airlines
Flight options found
52
Direct / non-stop options
7
Airport codes
Oakland–OAK, Chicago–MDW
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 Sat, 14 Nov found 52 flight options, 7 of them non-stop. The first flight leaves around 05:00 and the last around 23:39. The fastest flight takes about 4h 20m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Night from ₹12,322, Morning from ₹16,956, Afternoon from ₹16,956, Evening from ₹16,956. 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
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2
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5
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Why Book Your Flight with FlyX?
Compare the available Oakland to Chicago 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.
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Frequently Asked Questions
Is it worth booking Oakland to Chicago 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 Oakland to Chicago dates shown on this page, the lowest fare is on a Saturday at ₹12,322. This can change from week to week.
How far is Oakland from Chicago by air?
The direct air distance between Oakland (OAK) and Chicago (MDW) is about 2,961 km. Actual flight time varies with the routing the airline files and with winds on the day.
Is there a direct flight from Oakland to Chicago?
Yes. 7 non-stop flights are listed on this page for Oakland to Chicago, operated by American Airlines. Use the Stops filter to see only those.
Which airlines fly Oakland to Chicago?
American Airlines and Delta Air Lines are 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 Oakland to Chicago?
The quickest non-stop Oakland to Chicago flight on this page takes about 4h 20m. Non-stop flights here take between 4h 20m and 4h 38m. Journeys with a stop take longer, since the total includes the layover.
What is the cheapest Oakland to Chicago flight fare?
The lowest Oakland to Chicago fare on this page is ₹12,322. Fares on the same dates run up to ₹140,211, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.
Which is the cheapest airline for Oakland to Chicago flight?
On this page, Delta Air Lines has the lowest Oakland to Chicago fare, starting from ₹12,322. American Airlines is next, from ₹16,956. The cheapest airline can change with the date, so compare a few days around your trip.
What time do Oakland to Chicago flights depart?
On the dates shown here, the first departure is around 05:00 and the last around 23:39, local time at Oakland. 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 OAK–MDW, 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.
Planning more than the flight? Our United States guide covers the 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.
The OAK to MDW 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
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Lowest Oakland to Chicago airfare, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare
₹12,322
14/11/2026
Delta Air Lines
05:55
Cheapest Airfare Within 30 Days
₹12,076
27/11/2026
Delta Air Lines
05:55
Cheapest Airfare Within 90 Days
₹11,706
26/01/2027
Delta Air Lines
05:55
Book Oakland to Chicago Flight Tickets on FlyX
FlyX lists each Oakland to Chicago 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.
Oakland to Chicago Flight Distance, Duration and Time
The aerial distance between Oakland and Chicago is about 2,961 KM. In these results, journey times range from 4h 20m to 28h 56m. Flights with a layover take longer because the total includes the connection time.
Oakland to Chicago flight duration is approximately 4 hours 20 minutes non-stop. There are 7 non-stop Oakland to Chicago direct flights on the departure date shown on this page. Oakland to Chicago flight distance is around 2,961 KM.
Oakland to Chicago Flight Schedule and Timing
The search for these dates returned 52 flight options, 7 of them non-stop. The first departure from Oakland is at 05:00 and the last is at 23:39. Flights leave from Metropolitan Oak Intl and land at Midway.
Flight Route Details & Analysis
Flight Details
Information
Route
Oakland to Chicago
Aerial Distance
2,961 KM
Flight Duration
4h 20m - 28h 56m
Airport Codes
Oakland - OAK, Chicago - MDW
Total Flights Available
52 flights7 direct45 with layovers
First Flight Departure
Departs at 05:00
Last Flight Departure
Departs at 23:39
Early Morning Flights (12 AM - 8 AM)
18 flights2 direct16 with layovers
Morning Flights (8 AM - 12 PM)
10 flights1 direct9 with layovers
Afternoon Flights (12 PM - 4 PM)
18 flights2 direct16 with layovers
Evening Flights (4 PM - 8 PM)
5 flights1 direct4 with layovers
Night Flights (8 PM - 12 AM)
1 flight1 direct0 with layovers
Airport Information & Terminals
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.
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.
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Oakland to Chicago
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Metropolitan Oak Intl
