Northwest Chicago Holidays

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Top hotels in Northwest Chicago

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 S$176 per night from 17 May to 18 May
S$176
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (1,068 reviews)
The service was absolutely immaculate from start to finish. Every staff member was attentive, friendly, and made sure everything was perfect throughout the visit. The drinks were expertly made, flavorful, and beautifully presented. The atmosphere was warm, inviting, and had the perfect balance of ...

Reviewed on 10 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 S$203 per night from 25 May to 26 May
S$203
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,170 reviews)
Great everything!

Reviewed on 10 May, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$378 per night from 24 May to 25 May
S$378
24 May - 25 May
includes taxes & fees
8.4/10 Very Good! (2,289 reviews)
Trainee staff was really trying to get it right. Trainer was very good.

Reviewed on 10 May, 2026

Hilton Chicago O'Hare Airport
See all 4,011 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.