North Side Vacations from ￥379,826
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
￥379,826
per person
Oct 1 - Oct 8
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥500,735
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
2nd stay at the Kimpton Gray in Chicago and loved it! Service was exceptional! Felt like a guest at a family member’s home! Shout out to Savannah and Noah and the entire housekeeping team!
Reviewed on Aug 15, 2026
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
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.
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.
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.
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.
North Center
Get to know North Center and its many features like its bars and live music. You might want to explore sights like Martyrs' and Beat Kitchen, and you can jump on the metro at Addison Station (Brown Line) or Irving Park Station to get around the city.
Find the Best North Side Vacation Packages
North Side Hotel Deals
The Majestic Hotel
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
￥21,339
￥25,050 total
Aug 23 - Aug 24
includes taxes & fees
Hotel Lincoln
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
￥21,508
￥29,386 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,155 reviews)
"The rooms are so busted. No hot water,very low water pressure , peeling wallpaper, dusty Ac, rusted bath lights, cracking ceiling, cheap furniture, mattress so old u can feel the springs, old tv that barely worked , dirty accent chair, weird curtains that barely closed and attached to wall by a hook ..."
Reviewed on Aug 15, 2026
The Willows Hotel
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
￥18,123
￥21,274 total
Sep 9 - Sep 10
includes taxes & fees
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 North Side attractions
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.
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!
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.
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 acclaimed art scene in this vibrant area.
Armitage Avenue
During your trip to Chicago, you can do some window-shopping at Armitage Avenue. Stroll along the lakeside in this vibrant area, or check out its lively bars.
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.
Theater Wit
You can make plans for a show at Theater Wit during your stay in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
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 theater scene.
What to do in North Side
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
Frequently asked questions
How much does a North Side vacation package cost?
We make it simple to travel the world, with North Side vacation packages starting from just ￥379,826. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate escape, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to North Side?
Combining your hotel and flight with Expedia won't just save valuable time — it'll save you cash too. A North Side vacation package makes it a cinch to arrange your dream adventure. With more than 550 airlines around the world to choose from, finding flights that suit your schedule won't be an issue. On top of that, we've got over 1,000,000 hotels globally to pick from. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in North Side?
Most people who visit North Side put both Wrigley Field and McCormick Place on their must-see lists. Why not choose a hotel near these iconic attractions?
What are the top hotels in North Side?
Get your trip off to a great start by reserving a room at Hotel Zachary Chicago, a Tribute Portfolio Hotel. It's one of most sought-after properties in North Side. Another leading option is The Chicago Hotel Collection - Wrigleyville.
How far in advance should I book my North Side vacation?
Search Expedia to compare airfares as soon as you know your travel dates. In most cases, you can purchase a seat up to 12 months before departure. If it's too early for your preferred air carrier, or you have to book last minute, don't stress. Low prices to North Side sometimes occur within weeks of the date of departure.
What does an Expedia North Side travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is yours. Whether you're headed to North Side with the family or adventuring with your friends, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a North Side travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and land great discounts. Hotels aren't your only option, though. We've got oceanfront condos, cozy city apartments and even houseboats and castles!
Can I choose my airline with a North Side Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to select from across the world. With so much choice, finding the right carrier to get you to North Side will be a cinch.
If I'm not able to travel, can I cancel my North Side vacation package?
You can. We realize life happens, so we're here to help if you need to make changes to your North Side vacation package. It may be possible to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
Explore a world of travel with Expedia
- East Village Hotels
- Motels in Chicago
- Cheap Hotels in Buena Park
- Lakeview Hotels
- Hotels near Chicago's Mercury Theater
- Luxury Hotels in Wicker Park
- All-Inclusive Hotel Hotels in Buena Park
- Hotels near Riviera Theatre
- Green Hotels in Downtown Chicago
- Hotels near Belmont Station
- Hotels with Early Check-in in Wrigleyville
- Cheap Hotels in Lincoln Park
- Wicker Park Hotels
- Logan Square Hotels
- Hotels near Vic Theatre
- Hotels near Ann and Robert H. Lurie Children's Hospital
- Hotels near Fullerton Station
- Hotels near DePaul University-Lincoln Park
- Hotel with a Concierge Hotels in West Loop
- Rush and Division Hotels
- Hotels near Clark-Lake Station
- Luxury Hotels in Gold Coast
- Hotels near Water Tower Place
- Beach Hotels in Hermosa
- Inns in Fullerton Station
- Lakeshore East Hotels
- Luxury Hotels in Wrigleyville
- Aparthotels in Chicago Station
- Adventure Hotels in Downtown Chicago
- Shopping Hotels in Wrigleyville
- Hotels near Marina City
- Resorts & Hotels with Spas in Chicago
- Business Hotels in Old Town Chicago
- Historic Hotels in Downtown Chicago
- Hotels near Theater Wit
- Luxury Hotels in Lake View East
- Family Hotels in Gold Coast
- All-Inclusive Hotel Hotels in Hermosa
- Adults Only Resorts & in The Loop
- Hotels near Wrigley Field
- Aparthotels in Chicago Station
- Business Hotels in Downtown Chicago
- Houseboats in Chicago Station
- Cheap Hotels in Portage Park
- Luxury Hotels in Lincoln Square
- Luxury Hotels in Little Italy
- Hotels near Millennium Station
- Hotels near Cadillac Palace Theatre
- West Town Hotels
- All-Inclusive Hotel Hotels in Irving Park
- Hotels near Grand Station
- Luxury Hotels in Palmer Square
- 5 Star Hotels in Chicago
- Palmer Square Hotels
- Guest Houses in Chicago
- Hotels with Free Parking in River North
- Hotels with a Pool in Gold Coast
- Lake View East Hotels
- Hotels near Richard J. Daley Center
- Hotels near Union Park
- Old Town Triangle Hotels
- Hotels near Second City
- Gold Coast Hotels
- Aparthotels in Rush Street
- Cheap Hotels in Edgewater
- Hotels near 360 CHICAGO
- Hotels near Bally's Casino Chicago
- Lincoln Square Hotels
- Cheap Hotels in Palmer Square
- Ryokans in Chicago
- Hotels near Chicago History Museum
- Family Hotels in Logan Square
- Rogers Park Hotels
- Resorts in Belmont Station
- Cheap Hotels in Gold Coast
- Avondale Hotels
- Fulton Market Hotels
- Hotels near Washington Square
- Business Hotels in Avondale
- Lincoln Park Hotels
- Ukrainian Village Hotels
- Historic Hotels in Chicago
- Hotels near Aragon Ballroom
- Hotels near Chicago Station
- Hotels with Early Check-in in Gold Coast
- Pet-Friendly Hotels in Downtown Chicago
- Hotels near Carbide and Carbon Building
- Hotels near Lincoln Park
- Hotels with a Pool in Chicago
- Hotels near Oak Street Beach
- Motels in Southport Station
- Aparthotels in Argyle Station
- Aparthotels in Chicago Grand-Cicero Station
- Boutique Hotels in Downtown Chicago
- Cheap Hotels in Mayfair
- Luxury Hotels in Buena Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
