Northwest Side Holidays

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    Better together
    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
11 Aug - 17 Aug
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Lovely staff, nice room, and smells amazing.

Reviewed on 9 Jun 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
11 Aug - 17 Aug
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
11 Aug - 17 Aug
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,602 reviews)
Very pleased. Will stay again

Reviewed on 8 Jun 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
11 Aug - 17 Aug
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,750 reviews)
Small room was uncomfortable

Reviewed on 8 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
11 Aug - 17 Aug
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,757 reviews)
Great location! Comfy bed- pillows are amazing!

Reviewed on 10 Jun 2025

Where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.

Find hotels in Irving Park

Top hotels in Northwest Side

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is €183 per night from 30 Jun to 1 Jul
€183
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very Good! (4,177 reviews)
"Free breakfast. Clean rooms, great stay! No complaints."

Reviewed on 7 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €215 per night from 1 Jul to 2 Jul
€215
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,861 reviews)
"Great location and excellent staff. Enjoyed our stayed."

Reviewed on 8 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is €142 per night from 8 Jul to 9 Jul
€142
8 Jul - 9 Jul
includes taxes & fees
8.8/10 Excellent! (2,288 reviews)
"Pool not working"

Reviewed on 9 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,854 properties in Northwest 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.

Frequently asked questions

How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just €899. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Northwest Side?
Book everything all in one place with our Northwest Side holiday packages. We have deals on flights, hotels, tours and more that’ll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you’ll have the flexibility to mix and match as you like.
How far in advance should I book my Northwest Side holiday?
Savvy travellers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you’re late to book, don’t despair. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Northwest Side travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you’re headed to Northwest Side on a family road trip or travelling solo, there’s a package to fit every budget and style. Once you’ve made your booking, why not add on some activities?
Can I choose my airline with a Northwest Side Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Northwest Side holiday package?
Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

€43
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€40
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€29
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.