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.
OAKMDWSat, 03 Oct
Fare checked before payment No hidden charges Transparent cancellation policy 24×7 booking support
Lowest fareUS$243Delta Air Lines
Fastest9h 59mgate to gate
Options found12flights on this route
Find your flightOAK → MDW
Available Flights & Fares
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Prices in USD
12 flight options
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TownePlace Suites by Marriott Chicago Elgin-West Dundee
2185 Marriott Dr, 60118
Room availability is checked live
$81per night+ taxes if applicable
1 Night • 3 Star
3.0Very GoodLive availability
Hawthorn Suites by WY Chicago Schaumburg
1200 Bank Drive, 60173
Room availability is checked live
$85per night+ taxes if applicable
1 Night • 3 Star
3.0Very GoodLive availability
Hawthorn Suites by Wyndham Northbrook Wheeling
8000 Capitol Drive, 60090
Room availability is checked live
$86per night+ taxes if applicable
1 Night • 3 Star
4.0Very GoodLive availability
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr, 60532
Room availability is checked live
$87per night+ taxes if applicable
1 Night • 4 Star
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Today's Airfare Highlights
Selected flight highlights for 03 Oct 2026.
Lowest fare$243Delta Air Lines06:00
Earliest departure$243Delta Air Lines06:00
Shortest duration$243Delta Air Lines06:00
Night
00:00-05:59
No optionOpen full search for moreMorning
06:00-11:59
$243Delta Air Lines at 06:00Afternoon
12:00-17:59
$427Delta Air Lines at 12:39Evening
18:00-23:59
No optionOpen full search for more
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 03 Oct 2026. View all flights opens the complete search result.
Fares and hotel rates usually run higher around these dates. Booking earlier — or shifting a day or two — often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMonday · in 29 daysPeak
12OctColumbus DayMonday · in 29 daysPeak
12OctIndigenous Peoples' DayMonday · in 29 daysPeak
11NovVeterans DayWednesday · in 59 days
26NovThanksgiving DayThursday · in 74 days
25DecChristmas DayFriday · in 103 days
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here — check the exact date for your travel year.
Compare your journey
How to travel Oakland to Chicago
Every option we can actually book for you, compared on price and journey time.
OptionFromJourney timeAvailability
Connecting flight₹23,247Longer — includes a stop12 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 Oakland to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
DE
Delta Air Lines Flights
from $24312 flights
Fares from
$243
Non-stop
None in these results
Departures
12 — compare timings in the list above
Route Overview & Flight Facts
Fastest flight duration
9h 59m · Delta Air Lines
First departure of the day
06:00 · Delta Air Lines
Last departure of the day
17:00 · Delta Air Lines
Options in this snapshot
12
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
Around 12 flights appear in the dated route snapshot. Departures run through the day — the first flight leaves around 06:00 and the last around 17:00. The fastest flight takes about 9h 59m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Morning from $243, Afternoon from $427. 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 update continuously with airline inventory.
One-Way vs Round-Trip Fare Comparison
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Online Web Check-In & Boarding Pass
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How to Book Cheap Flights on FlyX
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Destination & City Travel Guide
About Chicago
Chicago, the most populous city in Illinois and the third most populous in the United States, is a bustling metropolis known for its iconic skyline, vibrant arts scene, and diverse neighborhoods. Often referred to as the Windy City, Chicago offers a blend of architectural marvels, cultural landmarks, and a dynamic urban atmosphere. From world-class museums to sandy beaches along Lake Michigan, Chicago is a city that captivates visitors with its charm and energy.
Read more about Chicago
Airports
Chicago is served by two major airports: • O'Hare International Airport (ORD) - Located approximately 18 miles northwest of downtown Chicago • Chicago Midway International Airport (MDW) - Situated about 10 miles southwest of the city center
Hotels and Restaurants
Chicago offers a wide range of accommodation options to suit every budget: • The Ritz-Carlton Chicago - Luxury hotel with stunning views of Lake Michigan • The Drake Hotel - Historic hotel with elegant rooms and top-notch service • Hotel Lincoln - Boutique hotel with a rooftop bar and quirky decor • HI Chicago Hostel - Budget-friendly option with modern amenities
When it comes to dining, Chicago is a food lover's paradise: • Alinea - Renowned for its innovative and artistic dishes • Lou Malnati's Pizzeria - Famous for its deep-dish pizza • Girl & the Goat - Popular spot for creative small plates • Portillo's - Iconic for its Chicago-style hot dogs
Transportation
Getting around Chicago is convenient with various transportation options: • Chicago Transit Authority (CTA) - Extensive network of buses and 'L' trains • Metra - Commuter rail system connecting the suburbs to the city • Taxis and Rideshares - Widely available across the city • Divvy Bikes - Bike-sharing program with numerous docking stations
Must-See Places
Chicago boasts numerous attractions that should not be missed: • Millennium Park - Home to the iconic Cloud Gate sculpture (The Bean) • The Art Institute of Chicago - Houses an impressive collection of artworks • Navy Pier - Entertainment hub with rides, restaurants, and shops • Willis Tower Skydeck - Offers breathtaking views from the 103rd floor • Museum Campus - Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
Climate
Chicago experiences a continental climate with distinct seasons: • Winter (December to February) - Cold and snowy, ideal for winter sports • Spring (March to May) - Mild temperatures and blooming flowers • Summer (June to August) - Warm and humid, perfect for outdoor activities • Autumn (September to November) - Cool and crisp, great for sightseeing
The best time to visit Chicago is during late spring to early autumn when the weather is pleasant and outdoor events are in full swing. Whether you're exploring its architectural wonders, indulging in its culinary delights, or enjoying its vibrant cultural scene, Chicago promises an unforgettable experience.
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. Across the dates currently loaded for Oakland to Chicago, Saturday shows the lowest fare at $243. That is an observed snapshot for these dates, not a rule that holds every 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.
Are there non-stop flights from OAK to MDW?
Not for the dates currently loaded - every Oakland to Chicago option showing right now has at least one stop. Non-stop service can differ by season and by day, so it is worth checking nearby dates before you decide.
Which airlines fly Oakland to Chicago?
Delta Air Lines is showing on this route for the dates currently loaded. 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?
Every option currently loaded has at least one stop, and the shortest total journey time is about 9h 59m including the layover. Non-stop service on this route can vary by season and by day.
What is the cheapest Oakland to Chicago flight fare?
The lowest fare showing on Oakland to Chicago for the dates currently loaded is $243. Fares on the same dates run up to $764, depending on airline, timing and fare type. Airline pricing moves continuously, so treat this as a dated observation rather than a fixed price.
What time do Oakland to Chicago flights depart?
For the dates currently loaded the first departure is around 06:00 and the last is around 17:00, 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.
Last checked .
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 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.
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 today, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare Today
$243
03/10/2026
Delta Air Lines
06:00
Cheapest Airfare Within 30 Days
$238
13/10/2026
Delta Air Lines
06:00
Cheapest Airfare Within 90 Days
$231
12/12/2026
Delta Air Lines
06:00
Book Oakland to Chicago Flight Tickets on FlyX
Planning to fly from Oakland to Chicago? FlyX lets you compare flight rates, airline timings, layovers, and baggage allowances all in one simple list. From quick non-stop routes to flexible connecting options, finding and booking cheap air tickets has never been easier.
Oakland to Chicago Flight Distance, Duration and Time
The aerial distance between Oakland and Chicago is approximately 2,961 KM. The flight duration ranges from 9H :59 M up to 32H :05 M depending on whether you book a non-stop flight or a connecting schedule with layovers.
Oakland to Chicago Flight Schedule and Timing
Around 12 flights operate on this route, providing plenty of choices for your travel window. The earliest morning flight departs from Oakland at 06:00, while the last night flight leaves at 17:00. Flights depart 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
9H :59 M - 32H :05 M
Airport Codes
Oakland - OAK, Chicago - MDW
Total Flights Available
12 flights (0 direct)
First Flight Departure
Departs at 06:00
Last Flight Departure
Departs at 17:00
Early Morning Flights (12 AM - 8 AM)
5 direct/indirect flights
Morning Flights (8 AM - 12 PM)
0 direct/indirect flights
Afternoon Flights (12 PM - 4 PM)
5 direct/indirect flights
Evening Flights (4 PM - 8 PM)
2 direct/indirect flights
Night Flights (8 PM - 12 AM)
0 direct/indirect flights
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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Metropolitan Oak Intl