Oakton Vacation Packages 2026 from $406

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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.

LondonHouse Chicago, Curio Collection by Hilton

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)

9.4/10 Exceptional! (3,881 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$424

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$421

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$409

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,347 reviews)

Well located with everything you need including bars and restaurants nearby. Right opposite the google office. It has a nice restaurant and bar downstairs and a couple of restaurants attached, including an omakase sushi restaurant which we went to - was amazing. Rooms are nice and spacious, very modern, although bathroom amenities are pretty light. Otherwise the room has everything you need including hairdryer, steamer, robes etc. hallway carpets definitely need changing but that’s being very particular. The passing trains are quite loud but they don’t run at night so sleep was uninterrupted. I would happily stay there again.

Reviewed on Oct 22, 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

$570

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,005 reviews)

Amazing hotel ! Would def stay again

Reviewed on Oct 23, 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 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

$108 nightly

$129 total

Nov 10 - Nov 11

Total with taxes and fees

8/10 Very Good! (10,096 reviews)

"The hotel itself is huge with the historic main room being spectacular. Our room was a hike to get to but very clean, newer vinyl flooring, newer paint. We needed a one night stay for an event further south in the city so it was perfect for that. The location is pretty wonderful with Buckingham fountain ..."

Reviewed on Oct 24, 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 22 - Nov 23

Total with taxes and fees

8/10 Very Good! (2,566 reviews)

"n/a"

Reviewed on Oct 24, 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$116 nightly

$138 total

Nov 22 - Nov 23

Total with taxes and fees

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.