Oakton Vacation Packages 2026 from $954

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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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$954

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Great staff, great place!

Reviewed on Aug 5, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$2,857

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$994

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Hotel was so comfortable and the staff was so kind and professional. The best breakfast buffet i have seen at a hotel. The location couldn’t have been any better.

Reviewed on Aug 8, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$1,720

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,664

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,631 reviews)

Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 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.

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 nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Oakton Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$117 nightly

$140 total

Sep 8 - Sep 9

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Aug 30 - Aug 31

Total with taxes and fees

8/10 Very Good! (1,958 reviews)

"Nice and clean property. Walkable. Close to the Red Line."

Reviewed on Aug 8, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$217 nightly

$255 total

Aug 30 - Aug 31

Total with taxes and fees

See all 4,580 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.