Oakland Vacations from $663

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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,250, price is now $663 per person
$663
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
This hotel was so nice. It is literally steps from Michigan Avenue and so convenient to walk anywhere. The hotel itself is modern, clean, and well taken care of. The only negative thing I can say is we went to the rooftop bar at 10:30 and they told us it was closed. It’s supposed to close at 11 and there were other people sitting outside still having drinks. That was disappointing but all of the other amenities this hotel offers is great. You get a free breakfast too that’s pretty decent. For the cost and location, this was excellent.

Reviewed on Sep 5, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,220, price is now $752 per person
$752
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.

Reviewed on Sep 4, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,980, price is now $1,221 per person
$1,221
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $768 per person
$768
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,896 reviews)
The staff makes this place wonderful. Its a beautiful property and that is second to how attentive the staff is.

Reviewed on Sep 5, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,578, price is now $1,069 per person
$1,069
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on Sep 4, 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
$170 nightly
The price is $200 total per night from Sep 23 to Sep 24
$200 total
Sep 23 - Sep 24
Total with taxes and fees
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
$178 nightly
The price is $209 total per night from Sep 14 to Sep 15
$209 total
Sep 14 - Sep 15
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $196 total per night from Sep 22 to Sep 23
$196 total
Sep 22 - Sep 23
Total with taxes and fees
The Wade
See all 4,499 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
Magnificent Mile - River North showing night scenes, a city and signage

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

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.