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

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from MDW to OAK starting at $123 One Way, $253 Round Trip

Prices starting at $253 for return flights and $123 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.

Wed, May 20 - Tue, May 26
MDW
Chicago
OAK
Oakland
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Oakland, returning Tue, May 26, priced at $253 found 6 days ago
Mon, Jun 1 - Sat, Jun 6
MDW
Chicago
OAK
Oakland
$281 Roundtrip, found 4 days ago
$281
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Jun 1 from Chicago to Oakland, returning Sat, Jun 6, priced at $281 found 4 days ago
Wed, May 20 - Tue, May 26
MDW
Chicago
OAK
Oakland
$286 Roundtrip, found 6 days ago
$286
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Oakland, returning Tue, May 26, priced at $286 found 6 days ago
Mon, Jun 1 - Sat, Jun 6
MDW
Chicago
OAK
Oakland
$288 Roundtrip, just found
$288
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Jun 1 from Chicago to Oakland, returning Sat, Jun 6, priced at $288 just found
Thu, May 28 - Mon, Jun 1
MDW
Chicago
OAK
Oakland
$291 Roundtrip, found 5 days ago
$291
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, May 28 from Chicago to Oakland, returning Mon, Jun 1, priced at $291 found 5 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
$119 nightly
The price is $136 total per night from Apr 22 to Apr 23
$136 total
Apr 22 - Apr 23
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! (2,409 reviews)
Quiet

Reviewed on Apr 21, 2026

The Marina Inn on San Francisco Bay
Sonesta Emeryville - San Francisco Bay Bridge

Sonesta Emeryville - San Francisco Bay Bridge

3 out of 5
5555 Shellmound Street Emeryville CA
$119 nightly
The price is $134 total per night from May 10 to May 11
$134 total
May 10 - May 11
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! (1,426 reviews)
Sonesta is a great hotel. The shower walls have some mold. Showers need cleaning and caulking.

Reviewed on Apr 21, 2026

Sonesta Emeryville - San Francisco Bay Bridge
Club Quarters Hotel in San Francisco

Club Quarters Hotel in San Francisco

4 out of 5
424 Clay St San Francisco CA
$126 nightly
The price is $148 total per night from Apr 26 to Apr 27
$148 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in San Francisco. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
9/10 Wonderful! (3,057 reviews)
Love the area. Safer than any other part of the city from out POV. Close to everything we wanted to do. Friendly staff.

Reviewed on Apr 21, 2026

Club Quarters Hotel in San Francisco
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
$112 nightly
The price is $129 total per night from Apr 26 to Apr 27
$129 total
Apr 26 - Apr 27
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! (4,497 reviews)
Clean room, kind and helpful staff.

Reviewed on Apr 21, 2026

DoubleTree by Hilton Hotel Berkeley Marina
Claremont Resort & Club

Claremont Resort & Club

5 out of 5
41 Tunnel Road Berkeley CA
$328 nightly
The price is $372 total per night from Apr 26 to Apr 27
$372 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this luxury hotel in Berkeley. Enjoy 3 outdoor pools, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property ...
9/10 Wonderful! (1,006 reviews)
Excellent

Reviewed on Apr 20, 2026

Claremont Resort & Club
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
$119 nightly
The price is $136 total per night from Apr 22 to Apr 23
$136 total
Apr 22 - Apr 23
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! (2,409 reviews)
Quiet

Reviewed on Apr 21, 2026

The Marina Inn on San Francisco Bay
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 Apr 22 to Apr 23
$91 total
Apr 22 - Apr 23
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 (2,251 reviews)
The air conditioning wasn't working, elevator take long to came down

Reviewed on Apr 16, 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
$119 nightly
The price is $136 total per night from Apr 22 to Apr 23
$136 total
Apr 22 - Apr 23
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! (2,409 reviews)
Quiet

Reviewed on Apr 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
$110 nightly
The price is $128 total per night from Apr 26 to Apr 27
$128 total
Apr 26 - Apr 27
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! (1,686 reviews)
There is not a free breakfast so take that off the list. The property is currently under construction so everything is not available. I will not step off the property for fear of being killed so we missed dinner. Everything else was OK 👍

Reviewed on Apr 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
$69 nightly
The price is $80 total per night from Apr 28 to Apr 29
$80 total
Apr 28 - Apr 29
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 ...
6.8/10 (1,318 reviews)
I have contacted this place multiple times. I would like my refund. Horrible condition, nothing like the picture

Reviewed on Apr 20, 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 Apr 26 to Apr 27
$144 total
Apr 26 - Apr 27
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! (1,003 reviews)
Internet was fast. Did not arrive with a vehicle so I cannot review parking

Reviewed on Apr 21, 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
$152 nightly
The price is $171 total per night from May 3 to May 4
$171 total
May 3 - May 4
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! (1,300 reviews)
Yes, the breakfast was very good. Unfortunately there were a lot of gnats or flies. But other than that, we were very impressed for such a crowded weekend.

Reviewed on Apr 21, 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 Apr 30 to May 1
$171 total
Apr 30 - May 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! (1,004 reviews)
Excellent location near Bay St. Emeryville mall and Tokyo Central market, and not far from Berkeley which was our destination. Good size room and comfortable bed and sofa. Excellent selection and delicious free breakfast. Will definitely stay here again next time we’re in the area!

Reviewed on Apr 21, 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
$112 nightly
The price is $129 total per night from Apr 26 to Apr 27
$129 total
Apr 26 - Apr 27
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! (4,497 reviews)
Clean room, kind and helpful staff.

Reviewed on Apr 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.