Oakton Vacations from $348
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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.
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $564, price is now $348 per person
$348
per person
Apr 3 - Apr 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.
Reviewed on Jan 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $671, price is now $400 per person
$400
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $673, price is now $416 per person
$416
per person
Apr 8 - Apr 11
just found
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Enjoyed the room. The staff could use a hug not the friendliest. The games our outdated. Seen many guest besides me decide to go play at the other area casino
Reviewed on Jan 1, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $922, price is now $572 per person
$572
per person
Mar 23 - Mar 26
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast
Reviewed on Jan 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
5 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,527 reviews)
THe staff was very efficient and professional and the breakfast was great.
Reviewed on Jan 13, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 25 to Jan 26
$105 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (3,708 reviews)
The staff was amazing and helpful. The room was very clean and the view was beautiful. Everything was so relaxing i hardly wanted to leave the room. I had the best sleep ever in the comfortable king size bed. The gym my great , hot towels, water and headphones to use on the equipment. I stayed for ...
Reviewed on Jan 13, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,062 reviews)
Helpful staff! Great view of the river from our room.
Reviewed on Jan 13, 2026
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.
Discover the most popular places to visit in Oakton
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% 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.