North Side Vacation Packages 2026 from $389

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The Latest North Side vacation packages

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

Chicago Lake Shore Hotel

Kenwood

Save 100% on your flight

$389

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7/10 Good! (1,004 reviews)

My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!

Reviewed on Sep 22, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$656

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

Stay One Chicago

Downtown Chicago

Save 100% on your flight

$1,088

per person

Nov 26 - Dec 1

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.8/10 Good! (12 reviews)

Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on Sep 20, 2026

Silversmith Hotel Chicago Downtown

Downtown Chicago

Save 100% on your flight

$816

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (2,381 reviews)

Clean rooms, great convenient location in the loop. Staff was friendly and helpful. Would stay here again.

Reviewed on Sep 22, 2026

Kinzie Hotel

Downtown Chicago

Save 100% on your flight

$543

per person

Nov 26 - Dec 1

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (2,169 reviews)

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Where to stay in North Side

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

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

6 out of top 10 points of interest in this area

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 cityscape with a dense urban area, a prominent train track, and a distant skyline of tall buildings.

Logan Square

Get to know Logan Square and its many features like its breweries and live music. You might want to explore sights like Concord Music Hall and Milwaukee Avenue, and you can jump on the metro at Logan Square Station or California Station (Blue Line) to get around the city.

A baseball stadium filled with spectators during a game.

Wrigleyville

You might enjoy the bars while in Wrigleyville. Wrigley Field is a notable sight, and you can get around town at Sheridan Station or Addison Station (Red Line) to see more of the city.

A pedestrian bridge with a cyclist, people walking, and buildings in the background.

Bucktown

Well-liked for its churches and architecture, Bucktown is worth a visit. Check out the variety of things to see and do like Milwaukee Avenue and Holstein Park Public Pool, and jump on the metro at Western Station (O Hare Branch) to get around the city.

A cityscape with a river, high-rise buildings, and a marina.

Avondale

Check out the restaurants during your time in Avondale. Hop around the Chicago area on the metro at Belmont Station (Blue Line) to see top sights like Milwaukee Avenue and Podlasie Club.

Stay near popular North Side attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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A sign for the Pritzker Family Children's Zoo surrounded by autumn foliage.

Lincoln Park Zoo

9.0/10 (1,096 reviews)

This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!

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A vintage car in a museum exhibit, a neon sign reading "GAS FOR LESS", and a historical mural on the wall.

Chicago History Museum

9.0/10 (37 reviews)

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

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A cityscape with a prominent clock tower, a mix of modern and historic buildings, and a dense skyline.

Park West

8.8/10 (12 reviews)

You can make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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Theater Wit

You can make plans for a show at Theater Wit during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

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Second City

9.6/10 (15 reviews)

You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

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Vic Theatre

You can get tickets for a performance at Vic Theatre during your trip to Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

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