Downtown Chicago Vacation Packages 2026 from $645

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 Downtown Chicago Vacation

Reserving a Downtown Chicago vacation package is a great way to get to know this unique neighborhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago vacation is a cinch with Expedia.

The Latest Downtown Chicago Vacation Packages

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$645

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,128 reviews)

The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.

Reviewed on Aug 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$795

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$745

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$709

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (157 reviews)

Beautiful room. Great location. Will be back.

Reviewed on Aug 22, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$970

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,638 reviews)

I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago

Reviewed on Aug 22, 2026

Things to do in and around Downtown Chicago

Downtown Chicago offers a vibrant mix of family-friendly activities and outdoor attractions, making it perfect for a city-themed vacation. Visitors can enjoy popular shopping areas, arena entertainment, and theaters, alongside fun activities like mini golf. With its welcoming atmosphere and numerous nearby attractions, Downtown Chicago promises an unforgettable experience for tourists looking to explore the heart of the Windy City.

Shopping

Experience the vibrant shopping scene in Downtown Chicago at Chicago Place Mall, featuring a mix of business and family vibes. Don't miss 900 North Michigan Shops for entertainment and city flair. For a unique experience, visit Maxwell Street Market, a bustling public market with a local feel.

Recreation

At Soldier Field, immerse yourself in the exhilarating sports atmosphere while enjoying outdoor activities. Experience the cultural charm of the Chicago Theatre, where captivating performances await. For a lively night out, visit the House of Blues Chicago, where soulful music and great food create an unforgettable entertainment experience.

Adventure

Experience the thrill at Amazing Chicago's Funhouse Maze, where adventure and family fun collide. For a scenic hike, explore the Salt Creek Trail, offering beautiful outdoor vibes. Alternatively, bounce into fun at Sky High Sports Niles, perfect for family-friendly activities and an adventurous atmosphere.

Nightlife

Experience the vibrant nightlife of Downtown Chicago at Dave & Buster's, where you can enjoy drinks and entertainment in a lively atmosphere. For a more intimate vibe, head to Kingston Mines or Blues on Halstead, both offering great live music and a romantic setting just a few miles away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Downtown Chicago

Downtown Chicago is perfect for family vacations and outdoor adventures, featuring iconic skyscrapers, urban parks, and historic buildings. Visitors can explore cultural attractions and enjoy family-friendly experiences along the scenic Chicago Riverwalk, which is a must-see. Dive into the vibrant city life and discover everything Chicago has to offer, from stunning sights to engaging activities that cater to all ages and interests.

Navy Pier: Experience the vibrant atmosphere at Navy Pier, where you can enjoy breathtaking views of Lake Michigan and the Chicago skyline. This lively destination features amusement rides, restaurants, and cultural attractions, making it a perfect spot for families and friends to gather and relax.
Michigan Avenue: Stroll along Michigan Avenue, known as the Magnificent Mile, where you'll find an array of high-end shops, dining options, and iconic landmarks. The bustling energy of this street captures the essence of Chicago's urban life, perfect for shopping and people-watching.
Millennium Park: Visit Millennium Park, an urban oasis showcasing stunning art installations like the Cloud Gate sculpture. With beautiful gardens and open spaces, it's ideal for outdoor activities, picnics, and enjoying live performances, making it a favorite for families and visitors alike.

Best time to go to Downtown Chicago

The best time to visit Downtown Chicago can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Downtown Chicago falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Downtown Chicago falls in January, visitor numbers are slightly low and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly	Average	Slightly Low

Tips to save on your trip to Downtown Chicago

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Downtown Chicago.
Consider traveling to Downtown Chicago during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Where to stay in Downtown Chicago

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

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.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Downtown Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$113 nightly

$135 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,288 reviews)

"Convenient to many attractions. Comfortable room. Fastest elevators! Favorite place to stay in Chicago!"

Reviewed on Aug 23, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$125 nightly

$148 total

Aug 31 - Sep 1

Total with taxes and fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (865 reviews)

"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"

Reviewed on Aug 21, 2026

Get rates

See all 1,607 properties in Downtown Chicago

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 Downtown Chicago attractions

A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

See properties

A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

See properties

A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

See properties

A park with walking paths, trees, and benches. In the background, there are tall buildings, including a prominent skyscraper.

Grant Park

9.2/10 (12,844 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

See properties

A busy urban street with a train crossing, tall buildings, and a tram.

Michigan Avenue

9.4/10 (15,813 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

See properties