Oakton Vacations

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Your Oakton Vacation

Experience all the fabulous things this neighborhood has to offer with a customized Oakton vacation package. However you imagine spending your days here, you'll find countless opportunities for adventure, relaxation and fun. Get your trip to Oakton off to a flying start with visits to some of its nearby attractions, such as Rivers Casino and Arndt Park. Expedia is here to help put your plans into action. Book your perfect Oakton vacation now.

The Latest Oakton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on May 13, 2024

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 hotel + flight trips 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
The price is $167 per night from May 27 to May 28
$167
$196 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $105 per night from May 27 to May 28
$105
$138 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $153 per night from May 27 to May 28
$153
$205 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,351 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Oakton vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Oakton from just $678. And the more you bundle, the more dollars you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Oakton?
Imagine all the fun things you could do in Oakton with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and extras into an Oakton vacation package. You have plenty of choice when you book with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1,000,000 properties around the globe. Whether you’re taking off with the entire family or adventuring alone, organizing a getaway to Oakton is better with a package.
Where should I stay in Oakton?
With interesting attractions like Holy Family Hospital and Holy Family in this area, look for a hotel positioned near either of them. Arndt Park is another sight in Oakton that people flock to.
How far in advance should I book my Oakton vacation?
You’ll be rewarded with the biggest variety and the lowest prices by booking your trip to Oakton nice and early. Air carriers tend to release flight tickets around 12 months prior to departure, so start locking things in as soon as you can. That being said, Expedia is dedicated to giving you the best bargains around, so it’s always a good time to book your dream vacation!
What does an Expedia Oakton travel package include?
From hotels and airfares to car rentals, Expedia can help you shape an Oakton package that’s right for you. Vacationing for a week or two? Give some thought to a rental car, hotel and flight bundle. If you’re taking a short break, a hotel and flight deal could be what you’re after. Tours and activities can be added after you’ve booked. Our packages make it easy to save and plan.
What should I know before booking an Oakton travel package?
So many places to go, so many things to experience. With a package, you’ll be able to check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with an Oakton Expedia vacation package?
With a vacation package, you’re in charge. Whether you’d like to fly to Oakton in coach or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners around the world.
If I'm not able to travel, can I cancel my Oakton vacation package?
Because we know life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you’ve booked your Oakton vacation package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Oakton

Image for Wrigley Field

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
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Six Flags Great America

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$229
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.