Oakton Vacations from $410
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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.
Four Seasons Hotel Chicago
Downtown Chicago
Price was $4,688, price is now $2,724 per person
$2,724
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Late on room service. Forgot items requested, making room service even later.
Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working.
Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view.
Also the wings from room service could be SOO muchh better. Thanks for taking all my money tho!
Reviewed on Aug 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,426, price is now $842 per person
$842
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
The hotel is beautiful. It has an amazing breakfast buffet, an amazing terrace with great drinks. The staff is super helpful and friendly. This hotel is a 10/10 for sure!
Reviewed on Aug 5, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $796, price is now $500 per person
$500
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,879 reviews)
Clean
Quick check in
Reviewed on Aug 4, 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
$157 nightly
The price is $186 total per night from Sep 1 to Sep 2
$186 total
Sep 1 - Sep 2
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $181 total per night from Aug 23 to Aug 24
$181 total
Aug 23 - Aug 24
Total with taxes and fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $244 total per night from Aug 29 to Aug 30
$244 total
Aug 29 - Aug 30
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
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.