Oakton Vacations from $524
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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 $4,658, price is now $2,714 per person
$2,714
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)
I’m from Chicago and I think. It’s the best hotel in the city
Reviewed on Aug 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $3,572, price is now $2,087 per person
$2,087
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Great location and breakfast. Clean and comfortable rooms. Highly recommend. The rooftop was closed due to weather unfortunately was looking forward to it but not their fault!
Reviewed on Aug 2, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,354, price is now $805 per person
$805
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of
Home.
Reviewed on Jul 29, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $950, price is now $569 per person
$569
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
This has been a pretty decent lodging option in Chicago for the past few years. I am concerned that some recent management decisions will make it a little less attractive in the future.
Reviewed on Aug 2, 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
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 17 to Aug 18
$181 total
Aug 17 - Aug 18
Total with taxes and fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$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
$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.