Near West Side Holidays from £797

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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,019, price is now £797 per person
£797
per person
20 Jan - 24 Jan
found 6 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,082, price is now £813 per person
£813
per person
20 Jan - 24 Jan
found 6 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on 5 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,018, price is now £1,528 per person
£1,528
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on 6 Nov 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £2,673, price is now £2,122 per person
£2,122
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,347, price is now £1,074 per person
£1,074
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Rooms were dated and carpeting was old. There was just a sense that it had seen better days. Beds were good. Would not stay in that neighborhood next time.

Reviewed on 6 Nov 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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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

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 refundable
The price is £98 per night from 23 Nov to 24 Nov
£98
23 Nov - 24 Nov
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
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 £91 per night from 22 Nov to 23 Nov
£91
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (2,794 reviews)
"Great location- fantastic restaurant- friendly staff"

Reviewed on 6 Nov 2026

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £153 per night from 26 Nov to 27 Nov
£153
26 Nov - 27 Nov
includes taxes & fees
9.2/10 Wonderful! (1,358 reviews)
"Staff was amazing"

Reviewed on 6 Nov 2026

The Emily Hotel
See all 4,583 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 £797, 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.

Stay near popular Near West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
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.