Near West Side Holidays from £1,493

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,264, price is now £1,493 per person
£1,493
per person
25 Jul - 1 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,403, price is now £1,632 per person
£1,632
per person
25 Jul - 1 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,577, price is now £1,802 per person
£1,802
per person
25 Jul - 1 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
This hotel gives that WOW factor. The hotel was built in the1920 and the details are breath taking. What an incredible experience spend that extra coin to get the river view. It was totally worth it. We had room service for breakfast just a classic breakfast and it was delicious.the robes /slippers were such a lush touch. Rooftop patio is amazing. It will get busy. I just wish that it was available to guests first. Cute vibe. The staff are amazing and so sweet! Everything we wanted to do was 15 minutes tops. Great location! We loved walking around the town! Take the architectural tour. All of the buildings are truly masterpieces. Thanks for such a wonderful experience we loved it so much!

Reviewed on 7 May 2026

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 £2,454, price is now £1,735 per person
£1,735
per person
25 Jul - 1 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on 6 May 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,059, price is now £1,499 per person
£1,499
per person
25 Jul - 1 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.

Reviewed on 7 May 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

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

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 £127 per night from 25 May to 26 May
£127
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,154 reviews)
Clean and spacious

Reviewed on 8 May 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 £116 per night from 25 May to 26 May
£116
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
Next to train station close to restaurant and shopping.

Reviewed on 6 May 2026

Holiday Inn & Suites Chicago - Downtown by IHG
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £194 per night from 25 May to 26 May
£194
25 May - 26 May
includes taxes & fees
9.2/10 Wonderful! (473 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

Level Chicago Fulton Market
See all 4,780 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 £1,493, 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

Aerial view of the iconic John Hancock Center and shimmering skyscrapers meeting the tranquil blue of Lake Michigan's shoreline, Chicago, Illinois, United States.

United Center

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

United Center

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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
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.