Oakton Holidays

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    Packages with flights are ATOL protected

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.
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,713
    £1,296
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,535 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,877
    £1,398
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 20 - Aug 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (490 reviews)
    "Great location to the red line and buses. Our kids loved the game room, pool, and basketball court."
    Reviewed June 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,964
    £1,495
    per traveller
    found 18 hours ago
    Level Chicago – Old Town
  • Dinner served
    Jul 30 - Aug 4

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £2,062
    £1,606
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Breakfast and dinner served
    Jul 30 - Aug 3

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,800 reviews)
    "Old hotel and rooms. All the outlets in our room were titled and so hard to plug things in them. The outlets near the nightstands on either sides can’t accommodate a charger because they’re stuck on the side of the nightstand between it and the side of the bed. Hairdryer so old and didn’t work. Check in was exactly at 4, they weren’t lenient when I showed up at 2:40."
    Reviewed June 10, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,701
    £1,330
    per traveller
    found 1 day ago
    Omni Chicago Hotel

Where to stay in Oakton

Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
Downtown Chicago

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

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,237 reviews)
"First, this is a historic hotel, and visitors should be aware that the rooms reflect the historic vibe. If you want modern, you need to stay down the street at the Hilton. The rooms were very cute and clean, and the tiling in the bathroom was beautiful. The hotel has a prime location with easy walking ..."

Reviewed on 10 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £142 per night from 1 Jul to 2 Jul
£142
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,551 reviews)
"Enjoyed our stay"

Reviewed on 10 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 28 Jun to 29 Jun
£136
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,643 reviews)
"The door to the restroom kept getting jammed and wouldn’t close properly. Our room also had no WiFi… the staff couldn’t figure out why it wasn’t working."

Reviewed on 10 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,648 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 . 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

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.