
North Side Vacations from $389
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest North Side vacation packages

Chicago Lake Shore Hotel
Reviewed on Sep 22, 2026

Level Chicago – Old Town
Reviewed on Sep 19, 2026

Stay One Chicago
Reviewed on Sep 20, 2026

Silversmith Hotel Chicago Downtown
Reviewed on Sep 22, 2026

Where to stay in North Side

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.

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.

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.

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.

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
Wrigley Field

Lincoln Park Zoo

Chicago History Museum

Park West
Theater Wit
Second City
Vic Theatre
Lincoln Hall
What to do in North Side

Chicago: Navy Pier Centennial Wheel Ticket
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
- Northalsted Hotels
- Hilton Hotels in Wrigleyville
- Marriott Hotels & Resorts Hotels in Wrigleyville
- Budget Hotels in Wrigleyville
- Motels in Chicago
- Cabins in Chicago
- Lakeview Hotels
- Wrigleyville Hotels
- Bucktown Hotels
- Lincoln Park Hotels
- Free Parking Hotels in Wrigleyville
- 5 Star Hotels in Old Town Chicago
- 4 Star Hotels in Wrigleyville
- Wicker Park Hotels
- Flights to Skokie
- Flights to Chicago
- Flights to O'Hare Intl.
- Flights to Evanston
- Flights to Rosemont
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from Atlanta (ATL) to Chicago (MDW)
- Air India Limited New Delhi (DEL) to Chicago (ORD) flights
- Delta Air Lines Atlanta (ATL) to Chicago (MDW) flights
- Flights to Oak Park
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Where to stay in Chicago
- Bellwood Vacations
- Visit Lincoln Park
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Where to stay in Cicero
- Visit United Center
- Where to stay in Oak Park
- Visit West Loop
- West Side All Inclusive Vacation Packages
- Visit Rush Street
- Schaumburg Vacations
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Lincoln Park
- Rosemont Vacations
- North Avenue Beach
- Where to stay in Niles
- Visit The Loop
- Montrose Beach
- Chicago Vacations
- Visit Uptown
- Where to stay in Evanston
- Bensenville Vacations
- Westchester Vacations
- Darien Vacations
- Chicago All Inclusive Vacation Packages
- Summit Vacations
- Where to stay in Oakbrook Terrace
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Central Chicago
- Visit Chicago
- Visit Downtown Chicago
- Where to stay in Bridgeview
- Visit Wrigleyville
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Glenview
- West Side All Inclusive Vacation Packages
- Visit Magnificent Mile
- Oak Park Vacations
- Wrigley Field
- Visit Streeterville
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Rosemont
- Chicago All Inclusive Vacation Packages
- Wrigleyville Vacations
- Car rentals near Wicker Park
- Enterprise Rental Cars in Lakeview
- Car rentals near North Center
- Avis Rental Cars in Lakeview
- Minivan Car Rentals in Chicago
- Car rentals near Ravenswood
- Hertz Rental Cars in Wrigleyville
- Car rentals near Lincoln Park
- SUV Car Rentals in Chicago
- Car rentals near Downtown Chicago
- Car rentals near Lakeview





















