North Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Vincent Ramundo

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top North Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,069, price is now CA $777 per person
CA $777
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Nice setup, courteous staff, wasn’t expecting to have to pay $100 deposit on top of the money I paid Expedia, also an additional fee of $17 that Expedia did not cover even though they summed up all the charges before our stay. Seems to be a consistent issue with Expedia.

Reviewed on Jul 15, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,260, price is now CA $1,510 per person
CA $1,510
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on Jul 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $1,458, price is now CA $1,029 per person
CA $1,029
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,088, price is now CA $780 per person
CA $780
per person
Sep 10 - Sep 13
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The staff was very friendly while providing excellent customer service. Our room and hotel were well maintained and clean. The daily breakfast and coffee provided was also very delicious

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

Lincoln Park

7 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.

Find hotels in Lincoln Park

Ready to book your vacation to North Side?

 

Choose your dates

North Side Hotel Deals

Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Aug 10 to Aug 11
CA $238
CA $315 total
Aug 10 - Aug 11
includes taxes & fees
Hotel Lincoln
The Majestic Hotel

The Majestic Hotel

3 out of 5
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Aug 10 to Aug 11
CA $177
CA $207 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"The staff was very friendly, check in/out was easy, and the hotel is very charming. The room was clean and comfortable, and the hotel was quiet. We parked in the loading zone to check in, and then they pointed us to a condo parking garage nearby which had valet service and in/out. The building itself ..."

Reviewed on Jul 13, 2026

The Majestic Hotel
The Willows Hotel

The Willows Hotel

3 out of 5
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Jul 27 to Jul 28
CA $214
CA $251 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"Great hotel, perfect area."

Reviewed on Jul 15, 2026

The Willows Hotel
See all 517 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular North Side attractions

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

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in North Side

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 CA $777. 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

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