Oakton Vacations from $457

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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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $786, price is now $457 per person
$457
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Beautiful new hotel, gorgeous rooftop with delicious food. Hotel staff are super friendly and helpful.

Reviewed on Sep 30, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,306, price is now $736 per person
$736
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,031, price is now $589 per person
$589
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on Sep 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,395, price is now $1,379 per person
$1,379
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!

Reviewed on Sep 28, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,091, price is now $648 per person
$648
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 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

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.

Find hotels in Downtown Chicago

Oakton Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Oct 26 to Oct 27
$179 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $163 total per night from Oct 27 to Oct 28
$163 total
Oct 27 - Oct 28
Total with taxes and fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on Sep 24, 2025

Freehand Chicago
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
$201 nightly
The price is $236 total per night from Oct 29 to Oct 30
$236 total
Oct 29 - Oct 30
Total with taxes and fees
8.4/10 Very Good! (5,017 reviews)
"staff friendly"

Reviewed on Sep 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,551 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Oakton

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

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

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
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.