Oakton Vacations from $356
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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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $567, price is now $356 per person
$356
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
2 adults staying in a room with double beds. Room wasn't that big. Didn't have a closet, buttons on the safe didn't work properly, there was no fridge in the room and there was no cleaning services provided without paying more. It was fine for us as we were only there to sleep, but would be pretty crammed if in a group of 3-4 people.
Location was great. Easily accessible by transit and close to the Bean, Boat tour and Art Institute.
Overall, found it was a good value considering price point of other comparable hotels, but don't expect any frills while staying.
Reviewed on Oct 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you
Reviewed on Oct 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $848, price is now $502 per person
$502
per person
Dec 31 - Jan 3
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Hotel was wonderful. The rooftop bar was great and the atmosphere was wonderful. Downside was the staff. Waiter was extremely busy. They must have been short on waiter but there were extra bartenders and bus people just standing around
Took 20 min just to be acknowledged, 35 min for our drink. We told him we were ready to order food and he said he would be back and took another 10 min. We asked for water and 2 shots of fire ball along with our 1st drinks and didn't get them till we got our food. Why he didn't ask other staff to deliver water or bring the shots (easier to make than my husbands beer and my martini) i don't know , but he would walk right by us over and over, not look at us or give a little, I'll be with you as soon as I can thing. We felt ignored. We spent over 3 hours at the rooftop and all we wanted was a drink and snack and then go to our room after a long day of traveling.
Reviewed on Oct 27, 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 10 to Nov 11
$126 total
Nov 10 - Nov 11
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
$122 nightly
The price is $145 total per night from Nov 22 to Nov 23
$145 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (2,606 reviews)
"Awesome stay"
Reviewed on Oct 27, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 23 to Nov 24
$138 total
Nov 23 - Nov 24
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
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.