Oakton Vacations from $278

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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 $477, price is now $278 per person
$278
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.

Reviewed on Jan 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $625, price is now $368 per person
$368
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $475, price is now $284 per person
$284
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating

Reviewed on Jan 17, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $604, price is now $364 per person
$364
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.

Reviewed on Jan 20, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $654, price is now $395 per person
$395
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!

Reviewed on Jan 10, 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 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
$89 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
Total with taxes and fees
8/10 Very Good! (9,799 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...

Reviewed on Jan 20, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
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! (2,555 reviews)
Did not have breakfast

Reviewed on Jan 19, 2026

Hilton 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
$106 nightly
The price is $124 total per night from Feb 9 to Feb 10
$124 total
Feb 9 - Feb 10
Total with taxes and fees
8.4/10 Very Good! (5,574 reviews)
It was clean room.. breakfast was good

Reviewed on Jan 21, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,852 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
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Oakton

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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
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
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

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
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.