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The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Chicago
4 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
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥26,799 per night from Jun 30 to Jul 1
¥26,799
per night
Jun 30 - Jul 1
8.4/10 Very Good! (1,985 reviews)
"convenient location in the area"
Reviewed on May 30, 2024
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥27,913 per night from Jun 5 to Jun 6
¥27,913
per night
Jun 5 - Jun 6
7.6/10 Good! (6,814 reviews)
"Be aware there is only Analog TV in the room"
Reviewed on May 29, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥26,807 per night from Jun 30 to Jul 1
¥26,807
per night
Jun 30 - Jul 1
8.6/10 Excellent! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."
Reviewed on May 28, 2024
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
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Six Flags Great America
4.5/5(347 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
McCormick Place
4.5/5(1,805 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
¥27,764
Per adult
76% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.