Parkside Holidays from £1,007

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Your Parkside Holiday

Book a custom holiday package to Parkside and prepare to experience this city on your own terms. Think about spending some time in the neighbourhood of Flossmoor, which is good for golfing and lots more. A trip to Parkside is an excellent opportunity to take in the sights. Be sure to stop by big-name attractions such as Hollywood Casino Amphitheatre, Odyssey Fun World and George Dunne National Golf Club. Expedia can help you escape the everyday. Tailor your holiday to Parkside to suit your style of travel, whatever that may look like.

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 £1,321, price is now £1,007 per person
£1,007
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,810, price is now £1,241 per person
£1,241
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,793, price is now £1,244 per person
£1,244
per person
16 Jun - 21 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,495, price is now £1,125 per person
£1,125
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,742 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.

Reviewed on 22 Apr 2026

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,431, price is now £1,113 per person
£1,113
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,018 reviews)
Clean comfortable room , staff helpful, breakfast standard and location good

Reviewed on 24 Apr 2026

Where to stay in Parkside

Find the best Parkside areas and neighborhoods for the activities you enjoy most. Learn more about Parkside
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 Parkside

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is £66 per night from 28 Apr to 29 Apr
£66
28 Apr - 29 Apr
includes taxes & fees
7.2/10 Good! (1,524 reviews)
Staff was great. There was mold in my bathroom. Good People working there though

Reviewed on 24 Apr 2026

Chicago Club Inn & Suites
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £92 per night from 20 May to 21 May
£92
20 May - 21 May
includes taxes & fees
8/10 Very Good! (1,842 reviews)
Room was clean. Neighborhood not the best but not unsafe

Reviewed on 24 Apr 2026

Sleep Inn Midway Airport Bedford Park
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is £106 per night from 10 May to 11 May
£106
10 May - 11 May
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
Clean room, great parking

Reviewed on 23 Apr 2026

DoubleTree by Hilton Chicago - Alsip
See all 1,000 properties in Parkside
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
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Family Friendly Holidays

Frequently asked questions

How much does a Parkside travel package cost?
The most affordable Parkside package is £1,007, so your dream holiday can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to tailor make a package that suits you.
If I'm not able to travel, can I cancel my Parkside travel package?
It is possible to cancel your Parkside booking if your plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Parkside?
Creating your own Parkside travel package with Expedia is a great way to save. We have over 550 partner airlines and 1,000,000 hotels around the globe. With such an extensive range to pick from, you'll have no difficulty putting together your dream getaway.
Does Expedia offer Book Now, Pay Later Parkside holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can book that well-deserved holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Parkside?
Choose a hotel within walking distance of Hollywood Casino Amphitheatre. This impressive sight is in the centre of the action and on the to-do lists of many tourists.
What are the top hotels in Parkside?
Lock in a room at La Quinta Inn & Suites by Wyndham Chicago Tinley Park. It's one of this area's most popular properties. Another top-rated option in Parkside is EVEN Hotel Chicago Tinley Park-Conv Ctr.
How far in advance should I book my Parkside holiday?
Your best bet is to book early. Airlines generally advertise flights around a year in advance, and this is an ideal opportunity to land some of the lowest prices. Boss just told you to take all your holiday days in a few weeks? That's fine too — Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Parkside travel package include?
Flights, car rentals and hotels — we bring you the best deals. All you have to do is decide on your favourite combination. Once you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to put together an unforgettable Parkside getaway.
What should I know before booking a Parkside travel package?
When you book your hotels, flights and car rentals together, you'll land great discounts. Whether you're planning a wilderness getaway in a cabin or would rather stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Parkside Expedia travel package?
Most definitely. We offer more than 550 partner airlines all over the world, so you can design your Parkside escape according to your style and budget.

Popular places to visit

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

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.