North Side Holidays from £741

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Top North Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,009, price is now £741 per person
£741
per person
16 Apr - 19 Apr
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great location, clean and very nice restaurant and bar.

Reviewed on 9 Mar 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 £2,198, price is now £1,482 per person
£1,482
per person
26 May - 31 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Such a beautiful hotel, exceptional staff, and they really took care of everything we needed. Amazing stay!

Reviewed on 15 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,475, price is now £1,717 per person
£1,717
per person
26 May - 31 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great

Reviewed on 12 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,385, price is now £972 per person
£972
per person
1 Jun - 4 Jun
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great stay! No complaints! Breakfast buffet was a great plus!

Reviewed on 15 Mar 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,837, price is now £2,176 per person
£2,176
per person
26 May - 31 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
We had everything we needed and more! Great location for shopping and viewing a the beautiful city of Chicago.

Reviewed on 13 Mar 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 featuring 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

North Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in North Side

Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £92 per night from 17 Mar to 18 Mar
£92
17 Mar - 18 Mar
includes taxes & fees
7.8/10 Good! (1,088 reviews)
Great botiqye hotel

Reviewed on 14 Mar 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 £95 per night from 17 Mar to 18 Mar
£95
17 Mar - 18 Mar
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Very friendly staff. We were treated wonderfully and were asked if everything was good whenever we came downstairs. Easy walking to everything in the area

Reviewed on 15 Mar 2026

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 £113 per night from 16 Apr to 17 Apr
£113
16 Apr - 17 Apr
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
The only issue was that they do not make up the room or change the towels unless you request it each day. Also, they provided only two sets of towels per room but my wife likes a second towel for her hair. You can get an extra towel but you have to request it each day. Other than that, it has a great ...

Reviewed on 13 Mar 2026

The Willows Hotel
See all 587 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

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

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 featuring interior views, a garden and flowers

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

£19
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£33
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£28
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 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. Flight-inclusive packages are ATOL protected.