Near West Side Holidays from £894

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,455, price is now £894 per person
£894
per person
3 Oct - 10 Oct
found 9 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on 21 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,643, price is now £1,044 per person
£1,044
per person
3 Oct - 10 Oct
found 9 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything about it. Amazing room, view and pool!

Reviewed on 20 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,875, price is now £1,232 per person
£1,232
per person
3 Oct - 10 Oct
found 9 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,663, price is now £1,115 per person
£1,115
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was £1,723, price is now £1,158 per person
£1,158
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on 18 Aug 2025

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

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 £154 per night from 1 Sept to 2 Sept
£154
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,392 reviews)
"Good experience with the staff"

Reviewed on 19 Aug 2025

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 £141 per night from 2 Sept to 3 Sept
£141
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"It's not right downtown but close enough... a good little walk to here and there... not bad. I'd stay again if opportunity arises"

Reviewed on 19 Aug 2025

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 £160 per night from 1 Sept to 2 Sept
£160
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (272 reviews)
"Enjoyed it"

Reviewed on 17 Aug 2025

Level Chicago Fulton Market
See all 4,739 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 £894, 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

United Center

United Center

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

The Chicago Helicopter Tour 25 Miles

Chicago Helicopter 25-Mile Tour for up to Three Passengers

£479
per traveller
Chicago Helicopter 25-Mile Tour for up to Three Passengers
Chicago: Fulton Market Donut Adventure with Tastings

Chicago: Fulton Market Donut Adventure with Tastings

£50
per adult
Chicago: Fulton Market Donut Adventure with Tastings
Chicago Local Brewery Expedition with Homemade Guacamole

Chicago Local Brewery Expedition with Homemade Guacamole

£47
per adult
Chicago Local Brewery Expedition with Homemade Guacamole
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.