Oakland Vacations from $233

Book a Hotel + Flight or Car together to unlock savings

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.
Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $359, price is now $233 per person
$233
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.

Reviewed on Jan 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $687, price is now $397 per person
$397
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amazing staff, very friendly, clean, comfortable, amazing breakfast.

Reviewed on Feb 1, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $473, price is now $294 per person
$294
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.

Reviewed on Jan 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $439 per person
$439
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $740, price is now $469 per person
$469
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 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 showing a city

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
$97 nightly
The price is $114 total per night from Feb 2 to Feb 3
$114 total
Feb 2 - Feb 3
Total with taxes and fees
8/10 Very Good! (9,826 reviews)
Awesome location

Reviewed on Jan 30, 2026

Congress Plaza Hotel
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
$103 nightly
The price is $120 total per night from Feb 8 to Feb 9
$120 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Feb 10 to Feb 11
$105 total
Feb 10 - Feb 11
Total with taxes and fees
8.6/10 Excellent! (2,269 reviews)
Loved it! Everything was near

Reviewed on Jan 31, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,811 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 featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Color Factory Chicago Ticket

Color Factory Chicago Ticket

$34
per adult
96% of travellers recommend
Color Factory Chicago Ticket
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.