Oakland Vacations from $570
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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 Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $873, price is now $570 per person
$570
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
Very dated property and room. The “self park” that was reviewed as a positive for others is across the street and $58 a night. Not so ideal. Otherwise location is fantastic
Reviewed on Jun 14, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,371, price is now $761 per person
$761
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Breakfast, staff, near everything
Reviewed on Jun 14, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $992, price is now $618 per person
$618
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that
Reviewed on Jun 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,511, price is now $966 per person
$966
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience
Reviewed on Jun 14, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,225, price is now $807 per person
$807
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on.
The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful.
Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.
Reviewed on Jun 8, 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
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,277 reviews)
"We able to checkin early for a small fee. Room was clean and good size. Shower was nice. Had shampoo conditioner and body wash. Sink was a little small for toiletries. Had a mini fridge and TV was fine. They stored our bags when leaving and concierge was very helpful. Very close to Millennial Park ..."
Reviewed on Jun 15, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
$146 nightly
The price is $174 total per night from Jun 30 to Jul 1
$174 total
Jun 30 - Jul 1
Total with taxes and fees
7.8/10 Good! (1,584 reviews)
"Room was great very spacious. Lots of places to shop short walk to navy pier. Plenty of places to eat"
Reviewed on Jun 14, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,670 reviews)
"The hotel itself is nice staff friendly but beware of parking costs and expensive breakfast buffet. Would stay again."
Reviewed on Jun 14, 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.
Stay near popular Oakland attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.