Oakton Holidays

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Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Price was S$2,686, price is now S$2,396 per person
S$2,396
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,201 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.

Reviewed on 9 Mar, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.

Reviewed on 11 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,002 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,908, price is now S$2,595 per person
S$2,595
per person
29 May - 31 May
found 1 day ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
In the picture it does look nice but it definitely has its cracks and damages. There was a couple areas in my room that were breaking down, many scratches on the floor, my push door was broke and my shower head seemed to not be working well but the maintenance man said it’s cause it needed to be clean. I believe it should’ve been clean before arrival and my pillow cases had stains on them as well. Bed was comfortable and lighting in bathroom was great and of course the view was great.

Reviewed on 11 Mar, 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 which includes 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

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 S$182 per night from 27 Mar to 28 Mar
S$182
27 Mar - 28 Mar
includes taxes & fees
8/10 Very Good! (9,945 reviews)
The room was very clean and the bed comfortable. Parking was a bit of a challenge but not unexpected based on location. Will likely visit again when business brings me to the area.

Reviewed on 12 Mar, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$233 per night from 30 Mar to 31 Mar
S$233
30 Mar - 31 Mar
includes taxes & fees
9.4/10 Exceptional! (3,512 reviews)
Loud. Unexpected fees. Staff constantly watching you for what.

Reviewed on 12 Mar, 2026

Hotel Riu Plaza Chicago
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 S$183 per night from 22 Mar to 23 Mar
S$183
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (5,728 reviews)
Breakfast menu had great options for a family of five. Room was clean. I really like being able to text someone from the front desk to get questions answered. The location is excellent as well. Will definitely stay here again.

Reviewed on 11 Mar, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,744 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.

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 S$2,396. 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

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
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$33
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.