Northwest Side Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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

    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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,478, price is now €964 per person
€964
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!

Reviewed on 26 Jan 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,410, price is now €1,005 per person
€1,005
per person
1 Apr - 7 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on 8 Jan 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,452, price is now €1,046 per person
€1,046
per person
1 Apr - 7 Apr
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on 18 Jan 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was €1,379, price is now €1,002 per person
€1,002
per person
1 Apr - 7 Apr
found 3 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on 26 Jan 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,665, price is now €1,225 per person
€1,225
per person
14 Mar - 18 Mar
found 17 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on 24 Jan 2026

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
EyeEm Custom Shoots Q4 2018

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 Addison Station (Blue Line) to get around the city.

Find hotels in Irving Park

Top hotels in Northwest Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €134 per night from 14 Feb to 15 Feb
€134
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,828 reviews)
Yes perfectly clean

Reviewed on 24 Jan 2026

Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is €105 per night from 5 Feb to 6 Feb
€105
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,587 reviews)
Great room. Great location. Everything was clean.

Reviewed on 23 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €132 per night from 11 Feb to 12 Feb
€132
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (3,232 reviews)
Perfect

Reviewed on 24 Jan 2026

Hotel Riu Plaza Chicago
See all 5,215 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.

Popular places to visit

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

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Northwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€25
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Northwest Side

Frequently asked questions

Can I cancel my flight booking to Northwest Side due to COVID-19?
Our Customer Service Portal is where you can find information about changing or cancelling your flight due to COVID-19. Before purchasing your tickets, it's smart to check the terms and conditions of your airfare too.
What's the best way to find cheap flights to Northwest Side that have flexible change policies?
We know that things can change from one minute to the next, so booking a flexible airfare with Expedia is always a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to Northwest Side is only a few clicks away.
What are some of the general tips for travellers to Northwest Side during the COVID-19 outbreak?
With the continuation of the COVID-19 outbreak, travelling now comes with more challenges than in the past. Cast your eye over these worthwhile tips before boarding your flight to Northwest Side:
  • Before you book a flight, check if any travel restrictions apply — in both your origin and destination. Get the latest updates by reviewing government and airport websites.
  • When you pass through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. This will need to be removed for screening.
  • To reduce handling during the screening process, place items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
  • If you're planning to take food through the security checkpoint, put it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA employee will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Northwest Side?
Arrange your ticket with American Airlines and then begin working on your Northwest Side itinerary. This popular carrier offers 13307 flights a month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Northwest Side?
An effective strategy for getting your hands on cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Northwest Side, then click on the "flexible dates" box for a list of prices for nearby days. Another good tip? Book ahead of time. For an idea of costs, was the lowest price for a flight to Northwest Side in the last seven days.
How much is a flight to Northwest Side?
If you were travelling one way from (), you could've nabbed a cheap ticket for in the last seven days. Round-trip flights to Northwest Side ranged from to during this same period.
What are the most popular airports to fly into in Northwest Side?
Get ready to pack your suitcase and jet into O'Hare Intl. Airport (ORD), Northwest Side's primary flight hub. Book a fare on one of the 33491 flights that land at this popular destination every month.
When is the cheapest time to fly to Northwest Side?
Fly out on a Tuesday to boost your odds of landing the cheapest flight to Northwest Side. Mondays are usually the second most affordable day to take off. Saturday is generally the most expensive day to fly anywhere.
How much is a plane ticket to Northwest Side?
In the last seven days, fares to Northwest Side fluctuated between and . The early bird catches the worm, so snap up a bargain today.
Which airlines with flights to Northwest Side employ COVID-19 cleanliness policies?
As travel bans start to lift, many airlines are now servicing flights with new strategies including physical distancing and staggered boarding and disembarkation. Here's what some carriers are doing to help combat 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.

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.