Oakton Vacation Packages 2026 from $376

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.

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$376

per person

Dec 21 - Dec 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,841 reviews)

I didn’t like the fact that they said I would get a discount on being a senior citizen. The party lied and price was more

Reviewed on Oct 20, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$783

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$542

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

The first room I checked in to had the door not flushly closing, and looked like someone had pried their way into the room. I checked in at 2:30am after driving from the Green Bay Packers football game in Green Bay, and they insisted that I check out at 11am. After two or three calls, they managed to delay it to 12:30pm. They want a $100 an hour for every hour you stay in the room after 11am and they very aggressively enforce it. I did not pay this amount and won't be staying at this hotel again and recommend that they change their customer service approach or clients will be choosing other hotels.

Reviewed on Oct 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$433

per person

Jan 7 - Jan 13

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$477

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 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 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 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 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

$107 nightly

$127 total

Nov 11 - Nov 12

Total with taxes and fees

8/10 Very Good! (10,176 reviews)

"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."

Reviewed on Oct 21, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$121 nightly

$143 total

Nov 11 - Nov 12

Total with taxes and fees

8/10 Very Good! (2,545 reviews)

"needs a major update. elevator is so tiny and there are chunks out of the wall covered by paint."

Reviewed on Oct 21, 2026

River Hotel

75 East Wacker Drive Chicago IL

$152 nightly

$181 total

Nov 1 - Nov 2

Total with taxes and fees

See all 4,687 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.