North Side Holidays from £1,297

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Top North Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
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
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The building and rooms were beautiful, and clean. You cannot beat the views of the lake and the night skyline. We had a problem with the elevator keycard access not working but security helped us out. My biggest gripe is not having more options to order for room service from ther hotel restaurant. We didnt want to pay $70 for two burgers, and we didnt want to go out after a long day of traveling. We did door dash pizza, and everything was fine. Other than that, it was a very nice stay.

Reviewed on 28 Jul 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on 21 Jul 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The room ended up being quieter than I would have expected since it’s right next to one elevator bank and across the hall from the other. I was told upon check in that they would move me to another room down the hall. When we came back at 4 I was told that there was no note for that request and that there were no more King rooms. Overall the room was fine, nothing special.

Reviewed on 28 Jul 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
It was a perfect overnight stay in Chicago. Easy accessibility, clean & helpful staff.

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 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 featuring a city and modern architecture

Lincoln Park

5 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 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 £117 per night from 26 Aug to 27 Aug
£117
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (1,018 reviews)
"Great"

Reviewed on 26 Jul 2025

The Majestic Hotel
Chicago Getaway Hostel

Chicago Getaway Hostel

2 out of 5
616 W Arlington Pl, Chicago, IL
8.8/10 Excellent! (1,110 reviews)
"I’ll miss you all!"

Reviewed on 26 Jul 2025

Get rates
Chicago Getaway Hostel
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £145 per night from 17 Aug to 18 Aug
£145
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (1,019 reviews)
"Absolutely loved staying here"

Reviewed on 22 Jul 2025

Hotel Lincoln
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.
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 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 fascinating museums.

Lincoln Hall

What to do in North Side

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

£31
per adult
86% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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 £1,297. 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.

* 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.