North Side Holidays from £1,346

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Top North Side Flight + Hotel Deals

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

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,758, price is now £1,346 per person
£1,346
per person
11 Jul - 18 Jul
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,759 reviews)
Upon arrival, the guest service agents were kind and attentive to guests, even while others waited in line, and were careful to give each guest their attention. With this location being in the heart of downtown, it was easy to walk to the theatre or enjoy a walk along the lake.

Reviewed on 30 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £4,095, price is now £2,776 per person
£2,776
per person
1 Jun - 8 Jun
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on 27 Apr 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
Price was £2,411, price is now £1,692 per person
£1,692
per person
11 Jul - 18 Jul
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.

Reviewed on 29 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,883, price is now £2,043 per person
£2,043
per person
11 Jul - 18 Jul
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back

Reviewed on 27 Apr 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £2,014, price is now £1,545 per person
£1,545
per person
11 Jul - 18 Jul
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.

Reviewed on 22 Apr 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

North Side Essential Information

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

Top hotels in North Side

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 25 May to 26 May
£113
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
First room was not cleaned at all. Second room moved to had hidden leftovers in the fridge. Also charged for 2 beers we did not drink.

Reviewed on 28 Apr 2026

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 £137 per night from 25 May to 26 May
£137
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,095 reviews)
Hotel staff awesome and very attentive to our needs. Would like to see a couple bottles of water in the room. There were none in the vending machine or the coffee shop during our visit.

Reviewed on 29 Apr 2026

Hotel Lincoln
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
3475 N. Clark St. Chicago IL
Fully refundableReserve now, pay when you stay
The price is £181 per night from 13 May to 14 May
£181
13 May - 14 May
includes taxes & fees
7/10 Good! (998 reviews)
This is a perfectly nice and cute hotel in a good location near the stadium. Apparently it is one of three locations across the city, and they all share CENTRALIZED guest services staff. Said another way, there is no staff onsite to help you with anything, including opening the front door. You have ...

Reviewed on 22 Apr 2026

The Chicago Hotel Collection - Wrigleyville
See all 562 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.
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Popular places to visit

Wrigley Field

Wrigley Field

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

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

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.

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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.