Oakton Vacations from $389
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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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $633, price is now $389 per person
$389
per person
Mar 31 - Apr 4
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $817, price is now $450 per person
$450
per person
Mar 31 - Apr 4
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
We always stay at RIU when we’re in Chicago. Best hotel in the city!
Reviewed on Jan 4, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $457 per person
$457
per person
Mar 31 - Apr 4
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Best hotel ive ever stayed in. Perfect location for moving around Chicago. Everyone helpful, had a great time.
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,048, price is now $647 per person
$647
per person
Mar 26 - Mar 29
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,053, price is now $657 per person
$657
per person
Mar 31 - Apr 5
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
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/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 12 to Jan 13
$105 total
Jan 12 - Jan 13
Total with taxes and fees
8.8/10 Excellent! (3,663 reviews)
The room was pretty clean and the staff was kind. I’d like the pool to be opened but it was been remodeling the last couple of times we’ve been there
Reviewed on Jan 4, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 12 to Jan 13
$192 total
Jan 12 - Jan 13
Total with taxes and fees
8.4/10 Very Good! (2,473 reviews)
Room was clean and spacious. I liked how unique the hotel was with its historical displays and the architectural elements that are still visible. The game room area is a great place for those looking for something to do while waiting on others.
Reviewed on Jan 4, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,209 reviews)
We loved the restaurant staff and options. Mrs. Rose and Tony.
Reviewed on Jan 2, 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
Michigan Avenue
4.5/5(332 reviews)
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.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
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.