Oakton Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
€1,400
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9/10 Wonderful! (1,489 reviews)
Nice room and great location…need a restaurant and real bar-bar is sort of open…would like to see it after they really rebrand everything
Reviewed on 4 Oct 2026
Stay One Chicago
Downtown Chicago
€2,032
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8/10 Very good! (14 reviews)
The instructions on how to access the room were excellent and the room was well maintained and well stocked. Excellent choice for the price and location.
Reviewed on 2 Oct 2026
Cambridge Inn on Main
€2,708
per person
17 Dec - 21 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (74 reviews)
Everything about this hotel was great! A very historic Boutique Hotel that takes you back in time! Each room has a theme of its own which is unique to the period. The owner was very friendly and made sure that I had everything that I needed to make my stay excellent! If you're ever in that area or even doing business in the Madison Wisconsin area you may consider taking an extra half hour to drive to this hotel and stay there. I don't think you'll be disappointed at all as a matter of fact I would be surprised if you didn't like it. I've been in hotels halfway around the world and I must say that next time I'm back in that area I will be staying here!
Reviewed on 4 Oct 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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Oakton
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€135
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,177 reviews)
"If you’re going to a bears game this place is amazing. About a 25 minute walk not horrible, bed was comfortable room was clean. Not haunted at all despite the rumors. Overall a great experience."
Reviewed on 5 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€176
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€123
9 Oct - 10 Oct
includes taxes & fees
8/10 Very good! (2,417 reviews)
"The staff was just blatantly unhelpful. The front desk was often unmanned and could not take requests whether it was for a checkout or to ask about how a food delivery had been misplaced. I’ve seen HolidayInns with better customer service."
Reviewed on 5 Oct 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.
Frequently asked questions
How much does an Oakton holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Oakton from just €1,400. And the more you bundle, the more dollars you save. The holiday 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 holiday 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, organising 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 holiday?
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 holiday!
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. Holidaying 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 holiday package?
With a holiday 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 holiday 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 holiday 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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.