Oakton Vacation Packages 2026 from $632

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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

$632

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,960 reviews)

Great location but the rooms are small and outdated

Reviewed on Sep 1, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$931

per person

Nov 3 - Nov 10

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Love the RIU! The room was spacious, clean and the staff is very welcoming. The RIU is centrally located within the downtown area. ( This was a huge plus) Take advantage of the breakfast on the 2nd floor! Great way to start your morning and get fueled up for the day! -Highly recommend the rooftop bar, but make reservations and ask for seating on the ledge bar for the best night time view experience. (Side note; the food is bar food and not really a place to have a good meal. But the drinks are fantastic and nonalcoholic are available) Tired at the end of the day…then go to the lobby bar have a drink and sit in the lounge and relax. Highly recommended the stay!

Reviewed on Sep 1, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$1,165

per person

Nov 3 - Nov 10

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,577 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,130

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,654 reviews)

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$783

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,339 reviews)

Love staying at the Emily! Everyone is always so friendly and helpful and the loft style rooms are super comfortable and spacious. The neighborhood has the best food and coffee of every type within walking distance and many clubs as well including Garcia's and Broken Hearts.

Reviewed on Aug 31, 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 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

$95 nightly

$113 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,244 reviews)

"Historic property in a great location. Our room was mostly updated, but bathroom had some water leaking on the floor from somewhere. Also couldnt find a thermostat for our room but temp was fine. Bed was comfy. Huge closet for some reason. Ice maker on our floor didnt work."

Reviewed on Sep 1, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$114 nightly

$135 total

Sep 7 - Sep 8

Total with taxes and fees

8/10 Very Good! (2,145 reviews)

"Keys"

Reviewed on Sep 1, 2026

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

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See all 4,560 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.