Oakton Holidays from £956

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Your Oakton Holiday

Book a customised Oakton holiday package that has everything you need and nothing you don't. Good for cafes, nature and bars and pubs, consider staying in the neighbourhood 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 holiday to Oakton to suit your style of travel, whatever that may be.

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,488, price is now £956 per person
£956
per person
13 Nov - 17 Nov
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,928, price is now £1,124 per person
£1,124
per person
25 Oct - 1 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
See my Google review. CBR.

Reviewed on 21 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,670, price is now £1,090 per person
£1,090
per person
25 Oct - 1 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet

Reviewed on 22 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,097, price is now £1,394 per person
£1,394
per person
25 Oct - 1 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 2025

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 £1,668, price is now £1,118 per person
£1,118
per person
25 Oct - 1 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug 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 featuring 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

Top hotels in Oakton

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 1 Sept to 2 Sept
£132
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 £165 per night from 14 Sept to 15 Sept
£165
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
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
The price is £133 per night from 3 Sept to 4 Sept
£133
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,652 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oakton travel package cost?
Get your credit card ready, because a trip to Oakton starts from an enticing £956. When you combine your flights, hotels and more into a travel package, you'll score the biggest bargains.
If I'm not able to travel, can I cancel my Oakton travel package?
Plans can change in a flash, so yes, you can. You may be able to cancel or change your Oakton travel package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your hotel, car rental company or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Oakton?
If you love amazing deals, bundle your bookings into an Oakton travel package. Whether you need flights, hotels, day tours or rental cars, you can browse and book them all in one place. You'll have endless choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 properties all over the world to select from. Fly with who you prefer, book a room where you like and save some cash — now that's the perfect escape!
Does Expedia offer Book Now, Pay Later Oakton holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book your dream getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday in multiple transactions.
  • Low deposit holidays: Pressing the "book now" button is much easier with this payment plan. Put down a small deposit on your escape and then get on your way.

Where should I stay in Oakton?
It makes sense to stay near the action. Many visitors favor hotels within easy reach of top attractions, like Rivers Casino, Arndt Park and Holy Family Hospital.
What are the top hotels in Oakton?
Wyndham Chicago OHare and Best Western Des Plaines Inn are among the most popular hotels in Oakton. Why not have a look at the rates and facilities at each and then make up your mind?
How far in advance should I book my Oakton holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, low prices to Oakton will sometimes occur in the weeks leading up to departure.
What does an Expedia Oakton travel package include?
That depends entirely on you. You can choose from a variety of Oakton bundles, such as a flight, hotel and rental car. You can also book a hotel with a flight, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Oakton holiday looks like, you're sure to save!
What should I know before booking an Oakton travel package?
You'll enjoy impressive savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste money or time? Whether you're organising a luxury romantic escape or an affordable family break, explore our travel packages today.
Can I choose my airline with an Oakton Expedia travel package?
Yes, the choice is all yours. We have access to over 550 partner airlines across the globe, so you can customize your Oakton getaway according to your needs and budget.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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 which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

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

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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. Flight-inclusive packages are ATOL protected.