North Side Holidays from £746

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top North Side Flight + Hotel Deals

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

Arlo Chicago

4 out of 5
Downtown Chicago
Price was £930, price is now £746 per person
£746
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Fantastic

Reviewed on 1 Nov 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,077, price is now £820 per person
£820
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
K

Reviewed on 1 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,087, price is now £836 per person
£836
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,233, price is now £959 per person
£959
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

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 £956, price is now £773 per person
£773
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

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
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

6 out of top 10 points of interest in this area

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 £124 per night from 22 Nov to 23 Nov
£124
22 Nov - 23 Nov
includes taxes & fees
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 £97 per night from 3 Nov to 4 Nov
£97
3 Nov - 4 Nov
includes taxes & fees
7.4/10 Good! (1,003 reviews)
"Beautiful hotel and room. Not having staff on premise is a pain. Communication on basics was missing (wifi, checkout, etc.). Neither us or our other friends staying there got the information needed for lock box or wifi/checkout."

Reviewed on 30 Oct 2026

The Chicago Hotel Collection - Wrigleyville
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 £103 per night from 23 Nov to 24 Nov
£103
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (1,037 reviews)
"it was an amazing stay. the room was so cute and honestly pretty spacious! for the price it was so good! the front desk staff was also very helpful with questions that i had as well"

Reviewed on 1 Nov 2026

The Majestic Hotel
See all 567 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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Stay near popular North Side attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
See properties

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in North Side

Frequently asked questions

How much does a North Side travel package cost?
Create unforgettable memories with our North Side travel packages, which start from a low £746. Select the flights and hotels that fit your travel plans. Then, add on some experiences or tours to cap off your unique getaway.
If I'm not able to travel, can I cancel my North Side travel package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your North Side travel package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge additional fees. Need more information? Check out our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to North Side?
If you love getting a great deal, bundle your bookings into a North Side travel package. Whether you're searching for flights, hotels, rental cars or activities, you can book everything in one place. You'll have endless choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotels around the globe to select from. Fly with who you want, check in where you like and save your hard-earned money — now that's the perfect escape!
Does Expedia offer Book Now, Pay Later North Side holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book an incredible getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budgets, so you can have that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in North Side?
Holiday makers come from all over the world to experience Millennium Park and Wrigley Field in North Side. Stay near these wonderful attractions and visit them at your leisure.
What are the top hotels in North Side?
If it's your very first time in North Side, book a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both hotels offer friendly service and are favourites among many travellers.
How far in advance should I book my North Side holiday?
Reserving your flights early with Expedia means one less thing to worry about. Many air carriers display prices up to 12 months in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to North Side occasionally appear a few weeks before departure.
What does an Expedia North Side travel package include?
Expedia has everything you need to book your North Side getaway, but how your package is structured is up to you. Choose from any combination of flights, rental cars and hotels. After some activities to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to match your needs.
What should I know before booking a North Side travel package?
Booking all the parts of your escape together is a great way to save. Bundle your airfares, rental cars and hotels into a handy package. But you're not restricted to hotels. Expedia has all kinds of properties, including holiday rentals such as mountain cabins and city apartments. Your choices are almost endless!
Can I choose my airline with a North Side Expedia travel package?
With a travel package, the choice is in your hands. Whether you're hoping to fly to North Side in first class or coach, simply choose from the available airline options. Expedia has access to over 550 partner airlines globally.

Explore a world of travel with Expedia

* 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.