North Side Vacations from $805

Book a Hotel + Flight or Car together to unlock savings

Photo by Vincent Ramundo
  • 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

The Latest North Side vacation packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$805
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$1,053
per person
Oct 7 - Oct 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$960
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The hotel was perfectly fine for a room price half the cost we paid

Reviewed on Sep 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$953
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on Sep 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$1,286
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
.

Reviewed on Sep 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to North Side
View all trips

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 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 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 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 Riverfront Plaza, and jump on the metro at Western Station (O Hare Branch) to get around the city.

Lake View East

Lake View East

While visiting Lake View East, you might make a stop by sights like TimeLine Theatre and Nettlehorst French Market.

Stay near popular North Side attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago

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.
See properties
A red barn with a white door, surrounded by a garden with various plants and flowers.

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!
See properties
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.
See properties
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.
See properties

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.
See properties

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.
See properties

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.
See properties

Lincoln Hall

You can enjoy a show at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in North Side

North Side Hotel Deals

Hotel Lincoln

Hotel Lincoln

1816 N Clark Street Chicago IL
$171 nightly
$201 total
Sep 9 - Sep 10
Total with taxes and fees
Hotel Lincoln
The Willows Hotel

The Willows Hotel

555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
$165 nightly
$194 total
Sep 28 - Sep 29
Total with taxes and fees
The Willows Hotel
The Majestic Hotel

The Majestic Hotel

528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
$163 total
Sep 8 - Sep 9
Total with taxes and fees
The Majestic Hotel
See all 521 properties in North Side
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.

Find the Best North Side Vacation Packages

North Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

More vacations you might like

Explore a world of travel with Expedia

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