Oakton Vacation Packages 2026 from $612

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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.

The Latest Oakton Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$612

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,553 reviews)

Ridiculous

Reviewed on Aug 22, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$801

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$780

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Great stay on the river!

Reviewed on Aug 23, 2026

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$629

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (157 reviews)

Beautiful room. Great location. Will be back.

Reviewed on Aug 22, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$665

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

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.

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.

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.

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.

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.

Oakton Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$113 nightly

$135 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,289 reviews)

"I wouldn't if I were you and I will leave it there!"

Reviewed on Aug 23, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$125 nightly

$148 total

Sep 8 - Sep 9

Total with taxes and fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$257 nightly

$302 total

Sep 18 - Sep 19

Total with taxes and fees

8.4/10 Very Good! (2,434 reviews)

"Snack staff were the highlight of the stay helpful and friendly. Checkout staff did not make eye contact and said go- not welcoming."

Reviewed on Aug 23, 2026

See all 4,583 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.