Oakton Vacations from $237

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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 - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice

Reviewed on Nov 1, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $3,257, price is now $1,529 per person
$1,529
per person
Dec 28 - Jan 3
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was $1,349, price is now $647 per person
$647
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
20/10 Exceptional! (2 reviews)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $486 per person
$486
per person
Dec 20 - Dec 23
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.

Reviewed on Nov 17, 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $743, price is now $400 per person
$400
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
18.8/10 Exceptional! (160 reviews)
I visited Cielo restaurant. 5 out of 10 Casino 5 out of 10 Hotel 8 out of 10

Reviewed on Nov 16, 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 showing a city

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.

Find hotels in Downtown Chicago

Oakton Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Dec 8 to Dec 9
$102 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,272 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $149 total per night from Nov 26 to Nov 27
$149 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints

Reviewed on Nov 16, 2025

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful

Reviewed on Nov 18, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,719 properties in Oakton
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.
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All Inclusive Vacations
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Oakton

Wrigley Field featuring cbd, a sporting event and a city

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.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.