Oakton Vacations from $337
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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Save 100% on your flight
Price was $569, price is now $337 per person
$337
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
Roman everything was clean everything was made that was all and it was very
Reviewed on Nov 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $677, price is now $426 per person
$426
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Excellent hotel in an excellent location. Close to all the attractions. Fabulous size room with the most comfiest bed! All the amenities you need are already in the room. Only complaint was the shower pressure was low. Other than that it was fabulous. Excellent breakfast included - fantastic selection! Would definitely recommend this hotel.
Reviewed on Nov 4, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa.
There was no housekeeping.
Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before you arrive!
There is no lobby, no where in the hotel to hang, no vibe. You are literally staying in a condo and have to exit the building and walk a few blocks to be anywhere. Maybe this is the new hotel experience, but for me, I still like some ammenities.
The room was fine
T
Reviewed on Nov 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
$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! (10,101 reviews)
"Amazing view of the city, lake, and park from the room!"
Reviewed on Nov 4, 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 9 to Nov 10
$138 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (2,653 reviews)
"We arrived at 3 am due to flight delays. There were nail clippings on the rug next to the bed. The bedside phone did not work. We didn't pay for the $79/night amenities package, and I could not even find hot water for tea. The front desk clerk said I could get hot water in the gym at the water machine ..."
Reviewed on Nov 4, 2026
River Hotel
75 East Wacker Drive Chicago IL
$106 nightly
The price is $127 total per night from Nov 15 to Nov 16
$127 total
Nov 15 - Nov 16
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.