Cheap flights from MDW to OAK (Midway Intl. to Oakland Intl.)

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Cheap Flights from MDW to OAK starting at $133 One Way, $272 Round Trip

Prices starting at $272 for return flights and $133 for one-way flights to Oakland Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 21 - Wed, Jul 29
MDW
Chicago
OAK
Oakland
$272 Roundtrip, found 1 day ago
$272
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Chicago to Oakland, returning Wed, Jul 29, priced at $272 found 1 day ago
Tue, Jul 21 - Wed, Jul 29
MDW
Chicago
OAK
Oakland
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Chicago to Oakland, returning Wed, Jul 29, priced at $277 found 1 day ago
Tue, Jul 21 - Wed, Jul 29
MDW
Chicago
OAK
Oakland
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Chicago to Oakland, returning Wed, Jul 29, priced at $278 found 1 day ago
Tue, Jul 21 - Wed, Jul 29
MDW
Chicago
OAK
Oakland
$282 Roundtrip, found 1 day ago
$282
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Chicago to Oakland, returning Wed, Jul 29, priced at $282 found 1 day ago
Thu, Nov 5 - Mon, Nov 9
MDW
Chicago
OAK
Oakland
$287 Roundtrip, found 3 days ago
$287
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 5 from Chicago to Oakland, returning Mon, Nov 9, priced at $287 found 3 days ago

Hotel Ideas near Oakland Intl.

Airport Hotels near Oakland Intl.

The Marina Inn on San Francisco Bay

The Marina Inn on San Francisco Bay

3.5 out of 5
68 Monarch Bay Dr San Leandro CA
$99 nightly
The price is $113 total per night from May 24 to May 25
$113 total
May 24 - May 25
Total with taxes and fees
Book a stay at this golf hotel in San Leandro. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (2,439 reviews)
"It was a nice stay. Pretty clean and comfy."

Reviewed on May 21, 2026

The Marina Inn on San Francisco Bay
Oakland Marriott City Center

Oakland Marriott City Center

4 out of 5
1001 Broadway Oakland CA
$127 nightly
The price is $148 total per night from May 30 to May 31
$148 total
May 30 - May 31
Total with taxes and fees
Book a stay at this golf hotel in Oakland. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,025 reviews)
"…"

Reviewed on May 19, 2026

Oakland Marriott City Center
Sonesta Emeryville - San Francisco Bay Bridge

Sonesta Emeryville - San Francisco Bay Bridge

3 out of 5
5555 Shellmound Street Emeryville CA
$149 nightly
The price is $167 total per night from Jun 5 to Jun 6
$167 total
Jun 5 - Jun 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Emeryville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,458 reviews)
"The bath tub was not clean a dirty ring around the tub"

Reviewed on May 20, 2026

Sonesta Emeryville - San Francisco Bay Bridge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Oakland

DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

4 out of 5
200 Marina Blvd Berkeley CA
$111 nightly
The price is $128 total per night from May 24 to May 25
$128 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Berkeley. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
8.2/10 Very Good! (4,631 reviews)
"The hotel rooms were in terrible shape for the price being charged per night. Bathroom needs significant upgrade. Water pressure from shower was poor, barely good temperature hot water. The pillows and bed were in horrible condition that I ended up with a sore right arm from the discomfort. Outside ..."

Reviewed on May 21, 2026

DoubleTree by Hilton Hotel Berkeley Marina
The Marina Inn on San Francisco Bay

The Marina Inn on San Francisco Bay

3.5 out of 5
68 Monarch Bay Dr San Leandro CA
$99 nightly
The price is $113 total per night from May 24 to May 25
$113 total
May 24 - May 25
Total with taxes and fees
Book a stay at this golf hotel in San Leandro. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (2,439 reviews)
"It was a nice stay. Pretty clean and comfy."

Reviewed on May 21, 2026

The Marina Inn on San Francisco Bay
Oakland Marriott City Center

Oakland Marriott City Center

4 out of 5
1001 Broadway Oakland CA
$127 nightly
The price is $148 total per night from May 30 to May 31
$148 total
May 30 - May 31
Total with taxes and fees
Book a stay at this golf hotel in Oakland. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,025 reviews)
"…"

Reviewed on May 19, 2026

Oakland Marriott City Center
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Hotels With Airport Transportation

Oakland Airport Executive Hotel

Oakland Airport Executive Hotel

3 out of 5
150 Hegenberger Rd Oakland CA
$79 nightly
The price is $91 total per night from May 24 to May 25
$91 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakland. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the clean rooms in our reviews. ...
5.8/10 (2,233 reviews)
"M"

Reviewed on May 21, 2026

Oakland Airport Executive Hotel
The Marina Inn on San Francisco Bay

The Marina Inn on San Francisco Bay

3.5 out of 5
68 Monarch Bay Dr San Leandro CA
$99 nightly
The price is $113 total per night from May 24 to May 25
$113 total
May 24 - May 25
Total with taxes and fees
Book a stay at this golf hotel in San Leandro. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (2,439 reviews)
"It was a nice stay. Pretty clean and comfy."

Reviewed on May 21, 2026

The Marina Inn on San Francisco Bay
Courtyard by Marriott Oakland Airport

Courtyard by Marriott Oakland Airport

3 out of 5
350 Hegenberger Rd Oakland CA
$95 nightly
The price is $110 total per night from May 31 to Jun 1
$110 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,666 reviews)
"The staff very helpful Pleasant"

Reviewed on May 21, 2026

Courtyard by Marriott Oakland Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Oakland Hotels

Imperial Inn

Imperial Inn

2.5 out of 5
490 West MacArthur Blvd Oakland CA
Stay at this hotel in Oakland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.8/10 (966 reviews)
"Booked a room for 5 people and there were only two beds. The bed sheets were dirty, as if someone had slept in them and then the beds were remade."

Reviewed on Sep 11, 2024

Get rates
Imperial Inn
Jack London Inn

Jack London Inn

2 out of 5
444 Embarcadero W Oakland CA
$71 nightly
The price is $83 total per night from May 27 to May 28
$83 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakland. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the ...
6.6/10 (1,365 reviews)
"A/C and heater did not work, floor was damaged and the room smelled like weed."

Reviewed on May 21, 2026

Jack London Inn
Marina Inn

Marina Inn

2 out of 5
975 University Ave Berkeley CA
$125 nightly
The price is $144 total per night from May 27 to May 28
$144 total
May 27 - May 28
Total with taxes and fees
Stay at this motel in Berkeley. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,010 reviews)
"Place is close to UC Berkley our intended Target for the trip. Had safe parking"

Reviewed on May 19, 2026

Marina Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Oakland

HYATT house Emeryville/San Francisco Bay Area

HYATT house Emeryville/San Francisco Bay Area

3 out of 5
5800 Shellmound Street Emeryville CA
$161 nightly
The price is $181 total per night from May 31 to Jun 1
$181 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Emeryville. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,313 reviews)
"everything is good except breakfast variety is few. Not too many choices,"

Reviewed on May 20, 2026

HYATT house Emeryville/San Francisco Bay Area
Hyatt Place Emeryville/San Francisco Bay Area

Hyatt Place Emeryville/San Francisco Bay Area

3 out of 5
5700 Bay Street Emeryville CA
$152 nightly
The price is $171 total per night from May 31 to Jun 1
$171 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Emeryville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,001 reviews)
"Nice clean room. Friendly staff."

Reviewed on May 19, 2026

Hyatt Place Emeryville/San Francisco Bay Area
DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

4 out of 5
200 Marina Blvd Berkeley CA
$111 nightly
The price is $128 total per night from May 24 to May 25
$128 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Berkeley. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
8.2/10 Very Good! (4,631 reviews)
"The hotel rooms were in terrible shape for the price being charged per night. Bathroom needs significant upgrade. Water pressure from shower was poor, barely good temperature hot water. The pillows and bed were in horrible condition that I ended up with a sore right arm from the discomfort. Outside ..."

Reviewed on May 21, 2026

DoubleTree by Hilton Hotel Berkeley Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MDW to OAK Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Chicago Airport to Oakland Intl. Airport (OAK)?
The terrific news is Southwest Airlines flies straight from Chicago to Oakland, so you won't have to worry about getting off the plane until you reach the terminal at OAK.
What is the shortest flight from Chicago Airport to Oakland Intl. Airport?
Make the most of the opportunity to sit back and relax on the flight from Chicago to Oakland. The quickest flight time from Chicago Airport to OAK is 6 hours and 28 minutes, which gives you lots of time to enjoy a red wine or lose yourself in a gripping novel.
How many hours flight from MDW to Oakland Intl. Airport?
From Midway Intl. Airport (MDW) to Oakland Intl. Airport (OAK), you'll be cruising the skies for approximately 6 hours and 34 minutes. Sit back, order a glass of wine and take out your noise-canceling headphones. It's time to binge-watch your favorite TV shows.
What airlines have the most flights from Chicago Airport to Oakland Intl. Airport (OAK)?
If you're on the lookout for a hassle-free trip, book your ticket with Southwest Airlines. This air carrier has 104 monthly flights from MDW to Oakland Intl. Airport (OAK) and is one of the top airlines servicing this route.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.