North Side Holidays

Photo by Vincent Ramundo

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Top Flight + Hotel Deals in North Side

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 €1,670, price is now €1,016 per person
€1,016
per person
29 Jul - 3 Aug
found 10 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great!

Reviewed on 19 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €2,088, price is now €1,072 per person
€1,072
per person
29 Jul - 3 Aug
found 10 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Very good Outstanding service

Reviewed on 19 May 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
Save 100% on your flight
Price was €2,197, price is now €1,315 per person
€1,315
per person
29 Jul - 3 Aug
found 10 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again.

Reviewed on 21 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,214, price is now €1,359 per person
€1,359
per person
29 Jul - 3 Aug
found 10 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,721 reviews)
Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again.

Reviewed on 21 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,250, price is now €1,436 per person
€1,436
per person
29 Jul - 3 Aug
found 10 hours ago
Return direct flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (1,864 reviews)
Great experience! Would stay here agin

Reviewed on 18 May 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(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 €106 per night from 27 May to 28 May
€106
27 May - 28 May
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Easy check in. Close parking"

Reviewed on 21 May 2026

The Majestic 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 €149 per night from 25 May to 26 May
€149
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,112 reviews)
"Second time staying here. Love this hotel. I do wish they could get reduced fee parking with the Chicago History Museum. We stayed 4 nights and parking was $160. That’s my only complaint!"

Reviewed on 21 May 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 €99 per night from 26 May to 27 May
€99
26 May - 27 May
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Love this cute little hotel!! Close to lots of yummy restaurants and walking distance to Lincoln Park zoo and Wrigley."

Reviewed on 20 May 2026

The Willows Hotel
See all 584 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

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

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 Park Conservatory

Lincoln Park Conservatory

This glass structure filled with exotic plants is the perfect place to spend a quiet afternoon.

Lincoln Park Conservatory

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.

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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.