Oakton Vacation Packages 2026 from $261

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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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$261

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,105 reviews)

Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$597

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,873 reviews)

Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security

Reviewed on Oct 26, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

$499

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$406

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (591 reviews)

The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

Pendry Chicago

Downtown Chicago

$374

per person

Dec 28 - Dec 31

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,163 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 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 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 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

$104 nightly

$124 total

Nov 22 - Nov 23

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

$122 nightly

$145 total

Nov 22 - Nov 23

Total with taxes and fees

8/10 Very Good! (2,601 reviews)

"Beautiful hotel, dated rooms."

Reviewed on Oct 26, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$107 nightly

$127 total

Nov 26 - Nov 27

Total with taxes and fees

8.8/10 Excellent! (5,573 reviews)

"Room was clean at check-in, and cleaned daily by the staff. Plenty to do nearby, can walk just about anywhere."

Reviewed on Oct 26, 2026

See all 4,728 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.