North Side Vacations from NT$29,422

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The Latest North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$43,745, price is now NT$29,422 per person
NT$29,422
per person
May 15 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Big shoutout to Marina. Thank you for the hospitality and being so kind and helpful to me during my stay. Chicago is great!!

Reviewed on 2026/3/30

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,227, price is now NT$35,716 per person
NT$35,716
per person
May 15 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Friendly staff, nice breakfast!

Reviewed on 2026/3/31

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$72,381, price is now NT$50,602 per person
NT$50,602
per person
May 15 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on 2026/3/31

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,844, price is now NT$43,198 per person
NT$43,198
per person
May 15 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.

Reviewed on 2026/3/29

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$49,006, price is now NT$34,831 per person
NT$34,831
per person
May 15 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 2026/3/9

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
4.5/5(326 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

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 NT$3,020 per night from Apr 1 to Apr 2
NT$3,020
NT$3,545 total
Apr 1 - Apr 2
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Cute hotel, but fairly noisy (radiators and squeaky floors), as it is an older property. Water and coffee available in the lobby, but no coffee/tea machine in the rooms. Many places to eat/drink nearby. Parking is on the roof of a building at the end of the street.$25/day.

Reviewed on 2026/3/28

The Willows Hotel
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,847 per night from Apr 1 to Apr 2
NT$2,847
NT$3,905 total
Apr 1 - Apr 2
includes taxes & fees
7.8/10 Good! (1,093 reviews)
Would not recommend

Reviewed on 2026/3/31

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 NT$3,573 per night from Apr 1 to Apr 2
NT$3,573
NT$4,194 total
Apr 1 - Apr 2
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Pretty cool, Cubs themed hotel (and I’m not even a Cubs fan) with accessible parking garage. Stocked mini bar that you can either charge to your room or pay cash at the desk. Close enough to walk to Wrigleyville. Only thing I didn’t enjoy was the creaky floors - you could hear the people on the floor ...

Reviewed on 2026/3/31

The Majestic Hotel
See all 585 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

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

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.