Northwest Chicago Holidays

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Northwest Chicago Holiday

Our pick of the best Northwest Chicago Hotel Deals

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is NZ$231 per night from 31 May to 1 June
NZ$231
31 May - 1 June
includes taxes & fees
8.8/10 Excellent! (1,059 reviews)
All good

Reviewed on 5 May 2026

Eaglewood Resort and Spa
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundable
The price is NZ$294 per night from 25 May to 26 May
NZ$294
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,148 reviews)
I travel to Chicago frequently, but I usually stay outside of the downtown area. I made an exception for this hotel as it was convenient to my event at the United Center. I was really impressed! The location was awesome, the entrance felt secluded, safe and not crowded yet walkable to dozens of restaurants, ...

Reviewed on 5 May 2026

Crowne Plaza Chicago West Loop by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is NZ$328 per night from 10 May to 11 May
NZ$328
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (2,531 reviews)
Wonderful staff

Reviewed on 5 May 2026

Hyatt Regency O'Hare Chicago
See all 4,012 properties in Northwest Chicago
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.

Discover the most popular places to visit in Northwest Chicago

Woodfield Mall

Woodfield Mall

5/5(1 review)

Browse through over 300 stores, restaurants and specialty shops at Schaumburg’s expansive shopping mall, one of the largest in the United States.

Woodfield Mall
Lynfred Winery

Lynfred Winery

You can enjoy a tasting or tour at Lynfred Winery during your travels to Roselle. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Lynfred Winery

Schaumburg Convention Center

Learn about the events happening in Schaumburg Convention Center during your trip to Schaumburg. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Schaumburg Convention Center

What to do in Northwest Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$46
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$75
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Northwest Chicago

Frequently asked questions

Can I cancel my flight booking to Northwest Chicago due to COVID-19?
Head to our Customer Service Portal for details about changing or cancelling flights because of COVID-19. Also, read through the terms and conditions of your preferred carrier before booking your fare to Northwest Chicago.
What's the best way to find cheap flights to Northwest Chicago that have flexible change policies?
We understand that things can change very quickly, so choosing a flexible ticket with Expedia is always a clever idea. Simply mark the "No change fee" box underneath the "Flexible change policies" filter. Your affordable, flexible flight to Northwest Chicago is just a few clicks away.
What are some of the general tips for travellers to Northwest Chicago during the COVID-19 outbreak?
If it's your first time travelling during COVID-19  you'll notice plenty of new rules and regulations in place. Follow these tips and make your journey to Northwest Chicago go off without a hitch:
  • Before you lock in a flight, check if any travel bans or restrictions apply — in both your destination and origin. Get the latest updates by reviewing government websites.
  • Wear a face mask even during airport screening. A TSA officer will ask you to adjust your mask for ID purposes.
  • To minimize the risk of cross-contamination, place your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your pass directly to a TSA agent.
  • One container of liquid hand sanitizer is now allowed in your carry-on baggage. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning.
  • Put any personal items (e.g, keys, phone and wallet) in your carry-on instead of a bin to minimize handling during the screening process.
  • Separate any food you're carrying for screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to handle and inspect your belongings.

Which airlines fly to Northwest Chicago?
Let American Airlines take you there. This top carrier lists 13307 flights each month to O'Hare Intl. Airport (ORD), a Northwest Chicago gateway.
How can I find cheap tickets to Northwest Chicago?
One of the best ways to get a hold of cheap tickets to Northwest Chicago is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll reveal the cheapest prices for nearby days. The best price for a flight to Northwest Chicago in the last seven days was . Booking well in advance will generally help you get an even better deal.
How much is a flight to Northwest Chicago?
If you were jetting one way from (), you could've landed a cheap ticket for just in the last seven days. Return flights to Northwest Chicago ranged from to during this same period.
What are the most popular airports to fly into in Northwest Chicago?
Start planning your Northwest Chicago trip by reserving one of the 33491 flights each month to O'Hare Intl. Airport (ORD). This is the region's main entry point.
When is the cheapest time to fly to Northwest Chicago?
Taking off on a Tuesday, followed by a Monday, is generally the best way to pick up the cheapest fare. Avoid weekends if possible, because Saturday is typically the costliest day. Spend the funds you saved enjoying yourself in Northwest Chicago instead!
How much is a plane ticket to Northwest Chicago?
In the last seven days, tickets to Northwest Chicago varied between and . Prices depend on the departure time, carrier, cabin class and how early the fare is booked.
Which airlines with flights to Northwest Chicago employ COVID-19 cleanliness policies?
As passengers and cabin crew start travelling again, many airlines have implemented physical distancing and other vital measures to help lessen the spread of COVID-19. Below are some of them:
  • 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.
  • Southwest Airlines - this airline is known for providing passenger masks 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.