North Side Holidays

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Top Flight + Hotel Deals in North Side

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,088, price is now €899 per person
€899
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,137 reviews)
Staff was great, very kind and helpful. The room was great. It was clean and tidy and I enjoyed the unique decor!

Reviewed on 26 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,246, price is now €980 per person
€980
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on 27 Oct 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,103, price is now €919 per person
€919
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on 20 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was €1,208, price is now €1,018 per person
€1,018
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Great accommodation, staff really nice, room was spacious and very clean. Perfect location to walk just about anywhere,

Reviewed on 27 Oct 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,158, price is now €985 per person
€985
per person
29 Dec - 2 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,994 reviews)
One person at front desk during checkin in the afternoon. Rooms are dates and not well maintained. Bathrooms lights are sunk in, reciept from previous guest shoved in. Toilet paper stuffed in peep hole.

Reviewed on 27 Oct 2025

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 a city and modern architecture

Lincoln Park

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

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Top hotels in North Side

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 €124 per night from 25 Nov to 26 Nov
€124
25 Nov - 26 Nov
includes taxes & fees
8.6/10 Excellent! (1,022 reviews)
Nice hotel. Quirky yet the rooms are clean, well appointed and the bed is very comfortable. We had the sun room suite and it was perfect. We would definitely stay there again

Reviewed on 20 Oct 2025

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 €127 per night from 18 Nov to 19 Nov
€127
18 Nov - 19 Nov
includes taxes & fees
8.4/10 Very Good! (1,024 reviews)
Center of many thing to do & parking was convenient

Reviewed on 20 Oct 2025

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 €151 per night from 25 Nov to 26 Nov
€151
25 Nov - 26 Nov
includes taxes & fees
7.6/10 Good! (1,041 reviews)
Brighten up rooms, dated and dark

Reviewed on 20 Oct 2025

Hotel Lincoln
See all 555 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Lincoln Park Zoo featuring land animals and zoo animals as well as a couple

Lincoln Park Zoo

4/5(27 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!

Lincoln Park Zoo
Lincoln Hall

Lincoln Hall

You can get tickets for a performance at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Lincoln Hall

What to do in North Side

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

€38
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€38
per adult
98% of travellers recommend
Chicago Sightseeing River and Lake Cruise
River tour boat in Chicago

Architecture River Tour

€42
per adult
96% of travellers recommend
Architecture River Tour
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 cancelling 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 travellers 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 holiday makers 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.

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