Near West Side Holidays from £1,068

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,259, price is now £1,068 per person
£1,068
per person
13 Jun - 17 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Staff was friendly and helpful. Room was clean and the bed was comfortable.

Reviewed on 23 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,374, price is now £1,524 per person
£1,524
per person
16 May - 23 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Room was clean. Staff was nice. Was able to hear people walking by our room which woke up my girlfriend in the middle of the night.

Reviewed on 23 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,000, price is now £2,229 per person
£2,229
per person
16 May - 23 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
You will never look at staying at a hotel the same again. Absolutely the best. The level of standard is unmatched. Not our first go around and definitely will continue visiting.

Reviewed on 21 Mar 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,706, price is now £2,096 per person
£2,096
per person
16 May - 23 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back.

Reviewed on 23 Mar 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,640, price is now £2,128 per person
£2,128
per person
12 May - 18 May
found 8 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (3,230 reviews)
Nice staff very clean

Reviewed on 23 Mar 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 featuring a city

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

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 £177 per night from 29 Mar to 30 Mar
£177
29 Mar - 30 Mar
includes taxes & fees
9.2/10 Wonderful! (1,334 reviews)
Great hotel and close to our dinner reservation.

Reviewed on 23 Mar 2026

The Emily Hotel
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 £110 per night from 29 Mar to 30 Mar
£110
29 Mar - 30 Mar
includes taxes & fees
9/10 Wonderful! (2,028 reviews)
First time in Chicago after a long time, will definitely come back to this hotel when I come back

Reviewed on 23 Mar 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 refundable
The price is £113 per night from 29 Mar to 30 Mar
£113
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
Good room all around. Was kept warm or cool depending on the preference at the time. Very spacious and nice location. Wish that the room had a microwave, but everything else was solid aside from that. Staff was very friendly and always helpful.

Reviewed on 23 Mar 2026

Holiday Inn & Suites Chicago - Downtown by IHG
See all 4,770 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.
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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 £1,068, 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

Chicago_UnitedCenter_6064077_01

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 fascinating museums.

United Center

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£19
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£33
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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.