Oakton Vacation Packages 2026 from $448

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.

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$448

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$852

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$735

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Gret location, nice room and nice staff. Not enough elevators so we ended up waiting far too long and then had to queeze in with too many others. Totally overpriced for what you get. Doesn't live up to the Trump standard.

Reviewed on Sep 14, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$922

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,012 reviews)

Great location, staff and amenities. The room I had was small yet fit my budget and had everything I needed. My only suggestion is to have 4 chairs per table in the breakfast/bar area.

Reviewed on Sep 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$955

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

The staff was very great. From valet. Front desk check in. Very clean and nice . Room was great clean and I loved the ac work very well that is on top of my list of things how great properties are were we stay . We had breakfast at the hotel and staff and food was amazing.😀.

Reviewed on Sep 13, 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

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$152 nightly

$181 total

Sep 27 - Sep 28

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

$164 nightly

$195 total

Sep 29 - Sep 30

Total with taxes and fees

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$164 nightly

$195 total

Sep 27 - Sep 28

Total with taxes and fees

8/10 Very Good! (10,240 reviews)

"Es un hotel viejo, pero muy céntrico, si lo que quieres es conocer Chicago"

Reviewed on Sep 13, 2026

See all 4,570 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.