Oakton Vacations from $503
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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 $790, price is now $503 per person
$503
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,054 reviews)
There was a bug in the bed, the bathroom was not properly cleaned, and the floors were dusty. We stayed one night of our three-night stay, and we left early. We could not continue to stay at the property. The air conditioning in the room was loud, and the cooling was sporadic.
Reviewed on Jul 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,114, price is now $657 per person
$657
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Fue solo una noche, pero todo fue 100/10.
Reviewed on Jul 30, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $756, price is now $511 per person
$511
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
The best three parts were: a wonderful bed, a clean room, and a great location. This great historic hotel needs a little freshening up. Fresh paint where needed, and the hallway carpets should be cleaned or replaced. Overall, a great hotel, and I will stay there on my next trip to Chicago.
Reviewed on Jul 30, 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
$145 nightly
The price is $172 total per night from Aug 30 to Aug 31
$172 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (10,362 reviews)
"Always love when I stay at the Congress"
Reviewed on Jul 30, 2026
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 10 to Aug 11
$181 total
Aug 10 - Aug 11
Total with taxes and fees
8/10 Very Good! (1,863 reviews)
"Towels and wash clothes leave white microfibers all over your skin and hair."
Reviewed on Jul 30, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$169 nightly
The price is $193 total per night from Aug 30 to Aug 31
$193 total
Aug 30 - Aug 31
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
$42
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.