Near West Side Holidays from £1,210

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Your Near West Side Holiday

Take all the stress out of planning your next adventure with a Near West Side holiday package. Take in the sounds and sights of this appealing neighbourhood and experience all it has to offer. Kick start your trip to Near West Side by heading to nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your dream Near West Side holiday may look like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was £1,475, price is now £1,210 per person
£1,210
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,033 reviews)
The room was large, clean, and comfortable. The blackout shades and space were highlights. There are only two things that would make me question staying here again… 1. We arrived early and our room wasn’t ready, which is no big deal, but they wouldn’t even let us use the pool while we waited on our room. In my extensive travels, I’ve never experienced that and it was a bummer for my daughter. 2. The price for parking is really high… $65 a day! I understand it’s located in Chicago, but it’s not even located within walking distance to downtown. If you figure in the room rate, with the parking fee, and Uber fees, it makes the nightly rate very high compared to other hotels located in the heart of downtown.

Reviewed on 21 Jun 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £2,134, price is now £1,673 per person
£1,673
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,241 reviews)
My fave Chicago stay

Reviewed on 19 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,469, price is now £1,948 per person
£1,948
per person
30 Jul - 3 Aug
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
hotel was immaculate and the people were amazing.

Reviewed on 20 Jun 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £2,049, price is now £1,665 per person
£1,665
per person
30 Jul - 3 Aug
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable. The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.

Reviewed on 21 Jun 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,888, price is now £1,547 per person
£1,547
per person
30 Jul - 3 Aug
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on 21 Jun 2026

Where to stay in Near West Side

Find the best Near West Side areas and neighborhoods for the activities you enjoy most. Learn more about Near West Side
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Near West Side

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 refundableReserve now, pay when you stay
The price is £139 per night from 1 Jul to 2 Jul
£139
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,272 reviews)
"The views & the convenience of getting to local places."

Reviewed on 22 Jun 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £143 per night from 1 Jul to 2 Jul
£143
1 Jul - 2 Jul
includes taxes & fees
8.8/10 Excellent! (1,039 reviews)
"Way overpriced for what you get."

Reviewed on 21 Jun 2026

Holiday Inn & Suites Chicago - Downtown by IHG
Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
Fully refundableReserve now, pay when you stay
The price is £114 per night from 5 Jul to 6 Jul
£114
5 Jul - 6 Jul
includes taxes & fees
8.2/10 Very Good! (1,104 reviews)
"A nice surprise! Enjoyed our stay. We will be back!"

Reviewed on 21 Jun 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
See all 4,798 properties in Near West 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Near West Side travel package cost?
Perhaps less than you might think — from a tempting £1,210, actually! By bundling hotels, flights and car rentals into a custom-made travel package, your trip to Near West Side is only clicks away.
If I'm not able to travel, can I cancel my Near West Side travel package?
Your situation can change without warning, so yes, you can. You may be able to cancel or change your Near West Side travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still cancel and rebook, but your airline, hotel or car rental company may impose a fee. Need more information? Visit our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Near West Side?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you dollars too. A Near West Side travel package makes it a cinch to put together the ideal trip. With more than 550 airlines around the world to choose from, finding convenient flights that suit your schedule won't be difficult. In addition to that, we have over 1,000,000 properties globally to select from. Now that's choice! Whatever your budget, Expedia puts more of the world within your reach.
Does Expedia offer Book Now, Pay Later Near West Side holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has worked out a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book an incredible getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all types of budgets, so you can book that well-earned holiday sooner.
  • Pay in instalments holidays: If you want to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Near West Side?
Travellers come from near and far to experience Millennium Park and Wrigley Field in Near West Side. Stay near these wonderful attractions to make sightseeing easy.
What are the top hotels in Near West Side?
Book a stay at Hyatt Regency Chicago. It's one of the neighbourhood's most popular hotels. Another top option in Near West Side is The Godfrey Hotel Chicago.
How far in advance should I book my Near West Side holiday?
While prices do change, we generally recommend booking your seats as early as possible. Most international airfares are available on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still be in luck. Cheaper tickets to Near West Side sometimes occur in the weeks prior to departure.
What does an Expedia Near West Side travel package include?
Hotels, rental cars and flights — you'll discover them all here. With Expedia, you can shape your Near West Side travel package the way you like it. All you have to do is decide exactly what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Near West Side travel package?
You can save a tidy sum by combining your airfares, hotels and rental cars. Once you've made your booking, you can add on things like tours and activities. Your next unforgettable holiday is only a couple of clicks away.
Can I choose my airline with a Near West Side Expedia travel package?
Most definitely. Expedia has more than 550 partner airlines to select from globally. With such a huge range of choice, finding the ideal carrier to fly you to Near West Side won't be hard.

Popular places to visit

A coastal cityscape with a prominent skyscraper, a marina, and a curved highway.

United Center

4.5/5(15 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.