Oakland Vacations from $230

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $380, price is now $230 per person
$230
per person
Dec 4 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
I retired from Sonesta working at the corporate office and the Allegro was one of my favorite properties. It is vintage Chicago and it is beautiful. Our room was very clean and it was quiet. The lobby is so pretty. Great area in the Theatre District and very walkable with great restaurants. We will be back again to enjoy this beautiful property. The team does a wonderful job.

Reviewed on Sep 19, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $268 per person
$268
per person
Dec 4 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast buffet was amazing. Staff was super friendly and attentive

Reviewed on Sep 17, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $759 per person
$759
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Nice area, easy to get to, close to things to do

Reviewed on Sep 18, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $713, price is now $457 per person
$457
per person
Dec 4 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
It was nice to be able to stay right at the airport when we had flown in from overseas on a long flight and then had to fly out early the next morning

Reviewed on Sep 18, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,024, price is now $664 per person
$664
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (294 reviews)
The staff are super friendly and helpful. The amenities are amazing and it’s so close to Fulton market restaurants and markets. Will definitely stay again.

Reviewed on Sep 19, 2025

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
$168 nightly
The price is $197 total per night from Sep 22 to Sep 23
$197 total
Sep 22 - Sep 23
Total with taxes and fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"

Reviewed on Sep 18, 2025

Congress Plaza Hotel
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $174 total per night from Sep 22 to Sep 23
$174 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (2,922 reviews)
"Cafe was convenient"

Reviewed on Sep 19, 2025

Warwick Allerton - Chicago
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $184 total per night from Sep 22 to Sep 23
$184 total
Sep 22 - Sep 23
Total with taxes and fees
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"

Reviewed on Sep 17, 2025

citizenM Chicago Downtown
See all 4,464 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

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.