North Side Vacation Packages

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Top North Side Vacation Deals

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

La Banque Hotel

4 out of 5
Price was CA $1,112, price is now CA $835 per person
CA $835
per person
May 28 - May 31
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (473 reviews)
Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous

Reviewed on Mar 1, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,978, price is now CA $1,326 per person
CA $1,326
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great service, loved this place.

Reviewed on Apr 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,370, price is now CA $1,624 per person
CA $1,624
per person
Jun 19 - Jun 23
found 24 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was very good. Enjoyed our room and how everything was clean. There was no microwave so don’t try to bring food if you need to reheat it. Fridge was also not strong to freeze my ice cream so be aware. All the staff were kind and helpful. Rooftop was beautiful but the glass floor was out of service. The hotel was close to Michigan Ave so heading to stores was a breeze. Overall, had an amazing time with my partner and would recommend reserving a room at this establishment.

Reviewed on Apr 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,717, price is now CA $1,923 per person
CA $1,923
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay

Reviewed on Apr 7, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was CA $1,520, price is now CA $1,126 per person
CA $1,126
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
Warwick Allerton is my favorite place to stay when visiting Chicago! Staying in the Gold Coast means walking distance from the restaurants, stores and other Chicago touristy things. Super close to Nordstrom, Tiffany, Ralph Lauren etc. 5 minute walk to Steak 48 for dinner & about a 15 minute walk to the Navy Pier! A Walgreens is also close by for any last minute needs or touristy things like magnets and keychains. This hotel was also very accommodating, clean and had super kind staff. Parking is simple.. either use valet at the hotel or the hotel next door’s parking garage!

Reviewed on Apr 7, 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

Lincoln Park

6 out of top 10 points of interest in this area
5/5(20 area reviews)

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.

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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 $147 per night from Apr 13 to Apr 14
CA $147
CA $208 total
Apr 13 - Apr 14
includes taxes & fees
7.8/10 Good! (1,086 reviews)
All excellent

Reviewed on Apr 9, 2026

Hotel Lincoln
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 $155 per night from Apr 13 to Apr 14
CA $155
CA $181 total
Apr 13 - Apr 14
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Will absolutely come back! This charming, boutique hotel is the best kept secret.

Reviewed on Apr 8, 2026

The Willows Hotel
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 $142 per night from Apr 13 to Apr 14
CA $142
CA $166 total
Apr 13 - Apr 14
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Great

Reviewed on Apr 8, 2026

The Majestic Hotel
See all 593 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
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Discover the most popular places to visit in North Side

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago History Museum

Chicago History Museum

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

Chicago History Museum
Lincoln Park Zoo

Lincoln Park Zoo

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!

Lincoln Park Zoo

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $61
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in North Side

Frequently asked questions

Can I cancel my flight booking to North Side due to COVID-19?
In these difficult times, many carriers are offering more flexibility. Head to our Customer Service Portal for details about canceling or amending your flight due to COVID-19.
What's the best way to find cheap flights to North Side that have flexible change policies?
We understand that travel schedules can change in the blink of an eye, so choosing a flexible fare with Expedia is a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to North Side is only a few clicks away.
What are some of the general tips for travelers to North Side during the COVID-19 outbreak?
With new COVID-19 safety measures to follow, travel looks a bit different in this day and age. Here are a few things to know before you hop on that plane to North Side:
  • Investigate if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so don't forget to check government advisories before booking.
  • When you go through airport screening, keep your face mask on. You will be asked to lower it briefly for ID purposes. Anyone refusing to wear a mask may be denied entry or boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. After that, hold it up for inspection.
  • You are now permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. You'll need to remove it for X-ray screening.
  • Remove personal items from your pockets, like your phone, keys and wallet, and put them in your carry-on instead of into bins. This will minimize handling during screening.
  • Separate any food you have for X-ray screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to North Side?
Let American Airlines take you there. This popular carrier provides 13307 flights a month to O'Hare Intl. Airport (ORD), a North Side gateway.
How can I find cheap tickets to North Side?
An effective strategy for nabbing cheap airfares is to be flexible with your dates. Begin with searching for your flight to North Side, then click on the "flexible dates" box for a list of prices for nearby days. Another helpful hint? Book in advance. To give you an idea of fares, was the best price for a flight to North Side in the last seven days.
How much is a flight to North Side?
One-way flights departing from () sold for as little as in the last seven days. During this period, the cost of a return airfare to North Side ranged between and . If you spot a good deal, book fast — these fares don't hang around.
What are the most popular airports to fly into in North Side?
North Side's primary gateway is O'Hare Intl. Airport (ORD). Get your exciting journey underway by locking in a seat on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to North Side?
If you can be flexible with your travel dates to North Side, depart early in the week. The most affordable day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the costliest day, with many vacationers preferring to fly on the weekend.
How much is a plane ticket to North Side?
Airfares to North Side varied from to in the last seven days. Generally, the quicker you book the better the deal.
Which airlines with flights to North Side employ COVID-19 cleanliness policies?
As travel borders start to open, most airlines have resumed services with new strategies including social distancing and staggered boarding and disembarkation. Here's what a number of carriers are doing to ease the spread of COVID-19:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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