Oakland Vacation Packages
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Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,634, price is now CA $1,131 per person
CA $1,131
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on Mar 10, 2026
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Price was CA $1,954, price is now CA $1,461 per person
CA $1,461
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,201 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.
Reviewed on Mar 9, 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
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.
Oakland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Apr 1 to Apr 2
CA $131
CA $154 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.
Reviewed on Mar 10, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $187 per night from Mar 24 to Mar 25
CA $187
CA $258 total
Mar 24 - Mar 25
includes taxes & fees
9.4/10 Exceptional! (3,509 reviews)
Clean, amazing terrace, bad and breakfast.
Reviewed on Mar 10, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CA $166 per night from Mar 22 to Mar 23
CA $166
CA $195 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (5,725 reviews)
Great location. Room was very hot. U can't switch heat to AC in the rooms. U just have to deal with what the hotel has it on. Also they would only give us one little fan to cool off. Not 2 which I'm sure they had plenty of. Other then that no complaints. They give a free happy hour with 2 free drinks ...
Reviewed on Mar 11, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Oakland
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.