Oakton Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

Top Holiday Package Deals in Oakton

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $909
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $983
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
CA $2,564
per person
Dec 13 - Dec 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
CA $1,021
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
CA $931
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Everything was awesome love this place

Reviewed on Oct 2, 2026

Where to stay in Oakton

Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
A busy city street with tall buildings, a bus, and cars.

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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Find hotels in Lincoln Park

Oakton Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $225
CA $267 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (5,462 reviews)
"The room and the facility were just right, and the location was lovely. But the best thing about the stay was the helpfulness and interest from the staff. From upgrading our room (to include the great view!), to helping us find one of the five Starbucks Roasterys in the world, and storing our luggage ..."

Reviewed on Oct 2, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $165
CA $196 total
Nov 2 - Nov 3
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $204
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,391 reviews)
"Great experience on my first trip to Chicago"

Reviewed on Oct 2, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,620 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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Family Vacations
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Golf Vacations
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Romantic Vacations
Ski Vacations
Ski 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 CA $909. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.