North Side Vacations from ₩593,376

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The Latest North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was ₩735,038, price is now ₩593,376 per person
₩593,376
per person
Apr 10 - Apr 12
found 14 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Room and customer service was great!

Reviewed on Jan 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩947,142, price is now ₩649,819 per person
₩649,819
per person
Apr 10 - Apr 12
found 14 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, comfortable and quiet.

Reviewed on Jan 30, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ₩1,298,201, price is now ₩981,072 per person
₩981,072
per person
Apr 10 - Apr 12
found 14 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ₩746,806, price is now ₩598,361 per person
₩598,361
per person
Apr 10 - Apr 12
found 14 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!

Reviewed on Jan 23, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩785,808, price is now ₩636,264 per person
₩636,264
per person
Apr 10 - Apr 12
found 14 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
clean nice room, comfy bed, really nice rainfall and handheld showers, nice bathroom products. good location

Reviewed on Jan 30, 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
Chicago which includes modern architecture and a city

Lincoln Park

6 out of top 10 points of interest in this area
4.5/5(320 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.

Find hotels in Lincoln Park

Find the Best North Side Vacation Packages

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 ₩138,909 per night from Feb 19 to Feb 20
₩138,909
₩188,283 total
Feb 19 - Feb 20
includes taxes & fees
7.6/10 Good! (1,070 reviews)
It nestled in a great location. I would stay here again. Tip: I booked a SpotHero to park for half the price the hotel was going to charge for the same parking lot.

Reviewed on Jan 23, 2026

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 ₩118,453 per night from Mar 2 to Mar 3
₩118,453
₩139,053 total
Mar 2 - Mar 3
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Room was clean and quiet. Staff was very friendly. No vending machines, but the honor bar was not crazy expensive 👍 Would stay here again.

Reviewed on Jan 24, 2026

The Majestic Hotel
Hotel Versey Chicago Lincoln Park

Hotel Versey Chicago Lincoln Park

3 out of 5
644 West Diversey Parkway Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩116,254 per night from Feb 9 to Feb 10
₩116,254
₩136,471 total
Feb 9 - Feb 10
includes taxes & fees
8.6/10 Excellent! (1,496 reviews)
Great location

Reviewed on Jan 30, 2026

Hotel Versey Chicago Lincoln Park
See all 605 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.

Discover the most popular places to visit in North Side

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Beautiful autumn colors surround modern architecture in Millennium Park, Chicago during a sunny day

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

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.