Oakton Vacations from $319
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Your Oakton Vacation
Book a customized Oakton vacation package that has everything you need and nothing you don't. Good for cafes, nature and bars and pubs, consider staying in the neighborhood of Rogers Park. There's loads to see and do during your trip to Oakton, including Rivers Casino and Arndt Park. Expedia has what you need to escape your daily routine. Tailor your vacation to Oakton to suit your style of travel, whatever that may be.
The Latest Oakton Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $462, price is now $319 per person
$319
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
The room was Actually very clean. Staff was very nice with patient & polite. Nice view. Plenty of restaurants and stuff to do. I would Definitely suggest valet parking $76 in & out because self parking is $65 with no in & out.
Reviewed on Nov 2, 2026
Level Chicago – Old Town
Downtown Chicago
Price was $601, price is now $411 per person
$411
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó
Reviewed on Nov 1, 2026
Where to stay in Oakton
Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
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.
Oakton Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,090 reviews)
"Very nice historic hotel but there are little things that need attention such as the wallpaper by the 7th floor elevator. Other than that the room was clean and the staff provided quality customer service."
Reviewed on Nov 3, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 4 to Nov 5
$138 total
Nov 4 - Nov 5
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $131 total per night from Nov 26 to Nov 27
$131 total
Nov 26 - Nov 27
Total with taxes and fees
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.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.