Northwest Side Vacations

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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
A city skyline with illuminated buildings, a river, and a bridge.

Irving Park

5 out of top 10 points of interest in this area
4/5(1 area review)

Irving Park is well-liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Irish American Heritage Center are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

Find hotels in Irving Park

Find the Best Northwest Side Vacation Packages

Northwest Side Hotel Deals

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 ₩208,765 per night from Jun 29 to Jun 30
₩208,765
₩248,201 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,153 reviews)
"Great location! Historic building. clean room. Good value. hallways and stairwell could use some additional care and attention. chipping paint and damaged doors."

Reviewed on Jun 21, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩239,536 per night from Jul 5 to Jul 6
₩239,536
₩284,783 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (4,454 reviews)
"It’s dated but nice"

Reviewed on Jun 21, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ₩197,559 per night from Jun 29 to Jun 30
₩197,559
₩234,877 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,605 reviews)
"Overall a very good hotel! Staff were friendly and helpful. The hotel is located beside Michigan Ave which gave us access to lots of shops and restaurants nearby without having to walk long distances. The view from our room was pretty good as well, giving us a look down the street. One of the concierges ..."

Reviewed on Jun 21, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 5,057 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.

Discover the most popular places to visit in Northwest Side

Navy Pier

Navy Pier

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

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

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 canceling 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 travelers to Northwest Side during the COVID-19 outbreak?
With the continuation of the COVID-19 outbreak, traveling 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 traveling 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.

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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.