Douglas Vacation Packages 2026 from $359

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Your Douglas Vacation

Make travel planning easier by locking in a vacation package to Douglas. We'll handle the small stuff, so you can focus on savoring everything this neighborhood has to offer. Wondering what to see and do during your trip to Douglas? Nearby attractions like Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Center are excellent places to start. No matter your travel goals or budget, booking your ideal Douglas vacation is easy with Expedia.

The Latest Douglas Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$359

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)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$550

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$684

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$882

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$492

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

A relatively new, modern hotel with very spacious rooms and an excellent location; it also features a pleasant rooftop area for a drink, offering a nice view.

Reviewed on Oct 18, 2026

Where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas

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.

Douglas Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$108 nightly

$129 total

Nov 11 - Nov 12

Total with taxes and fees

River Hotel

75 East Wacker Drive Chicago IL

$152 nightly

$181 total

Nov 1 - Nov 2

Total with taxes and fees

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$142 nightly

$169 total

Nov 2 - Nov 3

Total with taxes and fees

8/10 Very Good! (2,418 reviews)

"terrible service"

Reviewed on Oct 18, 2026

See all 4,662 properties in Douglas

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.

Stay near popular Douglas attractions

Illinois Institute of Technology

7.0/10 (4 reviews)

Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.

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Wabash Ave YMCA

You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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McCormick Tribune Center

You can find out about the history of Chicago when you stop by McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

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Ida B Wells House

You can find out about the history of Chicago with a stop at Ida B Wells House. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

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Southside Community Arts Center

Enjoy an outing to Southside Community Arts Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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Lake Meadows Park

Lake Meadows Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

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State Street Village

You can find out about the history of Chicago with a stop at State Street Village. Stroll along the lakeside or visit the notable monuments in this vibrant area.

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Robert W Roloson Houses

You can find out about the history of Chicago with a visit to Robert W Roloson Houses. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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Things to do

360 CHICAGO Observation Deck

$24

per adult

86% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour

$41

per adult

94% of travellers recommend

cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158

per adult

80% of travellers recommend

See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Douglas Vacations from $359

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Douglas Vacation

The Latest Douglas Vacation Packages

Sheraton Grand Chicago Riverwalk

Swissotel - Chicago

Level Chicago – Old Town

Four Seasons Hotel Chicago

Hotel Riu Plaza Chicago

Where to stay in Douglas

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Douglas Hotel Deals

Congress Plaza Hotel

River Hotel

The Chicago Hotel Collection - Magnificent Mile

Stay near popular Douglas attractions

Illinois Institute of Technology

Wabash Ave YMCA

McCormick Tribune Center

Ida B Wells House

Southside Community Arts Center

Lake Meadows Park

State Street Village

Robert W Roloson Houses

Things to do

360 CHICAGO Observation Deck

Wendella's 90-min Chicago River Architecture Tour

City Cruises Chicago: Lake Michigan Premier Dinner Cruise