Oakland Vacations from $249

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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $430, price is now $249 per person
$249
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (281 reviews)
From the time we came through the front door we were greeted with a smile can’t remember their names but very good customer service rooms were great housekeeping gave me what I needed everyone greeted us every time we enter the lobby area Mike an Ashley checked us out with smiles they took time and ask how was our stay very knowledgeable about the billing also breakfast was excellent everything and everyone was great Thank you Jacqueline Robinson

Reviewed on Oct 21, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $840, price is now $345 per person
$345
per person
Nov 24 - Nov 27
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Hotel in great location, would stay again

Reviewed on Oct 19, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $835, price is now $445 per person
$445
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!

Reviewed on Oct 22, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $612, price is now $334 per person
$334
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Everything was perfect. Will stay at Riu Plaza again.

Reviewed on Oct 24, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,108, price is now $610 per person
$610
per person
Jan 1 - Jan 4
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
10/10 Exceptional! (2 reviews)

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
$116 nightly
The price is $136 total per night from Nov 24 to Nov 25
$136 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (9,566 reviews)
absolutely loved the view from my room on the 14th floor

Reviewed on Oct 23, 2025

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
$139 nightly
The price is $163 total per night from Nov 23 to Nov 24
$163 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,948 reviews)
We didn’t know what to expect from a Holiday Inn in a tower and were pleasantly surprised. The building — hotel actually starts on the 15th floor — is like new and was very clean. The staff was universally friendly. The lobby floor has a grab-and-go food option available 24 hours and a nontraditional ...

Reviewed on Oct 20, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
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
$115 nightly
The price is $135 total per night from Nov 16 to Nov 17
$135 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,135 reviews)
Great

Reviewed on Oct 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,522 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
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.