Oakton Vacation Packages 2026 from $575

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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.

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$575

per person

Dec 8 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (178 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$604

per person

Oct 29 - Nov 2

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

👍

Reviewed on Sep 28, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$728

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,340 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$587

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,025 reviews)

The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on Sep 29, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$741

per person

Oct 29 - Nov 2

found 14 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (527 reviews)

The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 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

$186 nightly

$221 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (5,464 reviews)

"Toilet was running all three nights, dirty room and super rude and loud people next door. Ridiculously small room with only one mirror in bathroom and nowhere to put our luggage not even a dresser"

Reviewed on Sep 29, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$157 nightly

$187 total

Oct 26 - Oct 27

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

$179 nightly

$213 total

Oct 25 - Oct 26

Total with taxes and fees

8/10 Very Good! (2,384 reviews)

"When you are told at check-in there is no housekeeping your stay doesn’t get off to a great start. The location of the hotel is great. This used to be a great hotel. We had 6 bags and there was no one to help get them to the room. The room was very sparse .. a large white box. When we checked out ..."

Reviewed on Sep 29, 2026

See all 4,585 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.