Oakland Vacations from $274

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Your Oakland Vacation

With a tailor-made vacation package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighborhood. From its nature to its walking, there's plenty to discover here. Kick start your trip to Oakland by heading to nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel goals or budget, booking your ideal Oakland vacation is easy with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $435, price is now $274 per person
$274
per person
May 19 - May 23
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (508 reviews)
The room was perfect but there was NO hot water

Reviewed on Apr 13, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $748, price is now $385 per person
$385
per person
May 17 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
They need to update the lobby real bad. Location is convenient a short walk to Willis Tower and you can self park very close.

Reviewed on Apr 3, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,183, price is now $651 per person
$651
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The breakfast was really good. It was like the Spanish meal, including smoked salmon, Jamon, and so on. The quality was impressive.

Reviewed on Apr 16, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,356, price is now $810 per person
$810
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
Very clean and nice place

Reviewed on Apr 16, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $827, price is now $511 per person
$511
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,241 reviews)
We were very happy with our stay to include the cleanliness, breakfast and the room overall.

Reviewed on Apr 11, 2026

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Oakland Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,153 reviews)
It’s in a great location and the staff is always nice.

Reviewed on Apr 15, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (4,129 reviews)
Loved the suite, connecting rooms! Needs a bit of renovating for rugs and wood! No room service!! Ok lobby.

Reviewed on Apr 15, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (5,844 reviews)
Super Family friendly, and right in the heart of dt Chicago great stay for pricing

Reviewed on Apr 16, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,638 properties in Oakland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Oakland

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.