Jackson Park Highlands Holidays from £843

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Your Jackson Park Highlands Holiday

Uncovering all that Jackson Park Highlands has to offer is easy when you book a Jackson Park Highlands holiday package. Well known for its history and more, this intriguing neighbourhood is calling your name. Some top nearby attractions to check out during your trip to Jackson Park Highlands include University of Chicago, Chicago Museum of Science and Industry and Robie House. No matter what your ideal Jackson Park Highlands holiday may look like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on 14 Apr 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on 20 Apr 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (650 reviews)
Great customer service

Reviewed on 21 Apr 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
Very very good experience. Stuff’s are friendly

Reviewed on 29 Apr 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
6 Jun - 9 Jun
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Where to stay in Jackson Park Highlands

Find the best Jackson Park Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Jackson Park Highlands
Downtown Chicago featuring a city

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 Jackson Park Highlands

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 30 Apr to 1 May
£115
per night
30 Apr - 1 May
7.6/10 Good! (2,534 reviews)
"My stay was very wonderful and pleasant"

Reviewed on 27 Apr 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £121 per night from 1 May to 2 May
£121
per night
1 May - 2 May
7.6/10 Good! (6,604 reviews)
Good but could be more comfy
"The rooms were updated but the mattress was not very comfortable."

Reviewed on 28 Apr 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £142 per night from 30 Apr to 1 May
£142
per night
30 Apr - 1 May
8.6/10 Excellent! (2,822 reviews)
"Small room is my only complaint, seems they cut the room in half, other that that room was quite and dining options around hotel were good"

Reviewed on 27 Apr 2024

River Hotel
See all 3,822 properties in Jackson Park Highlands
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 Jackson Park Highlands travel package cost?
The cheapest Jackson Park Highlands travel package is £843, so your dream trip can become a reality — without it costing a fortune. Combine flights, hotels and car rentals to customize a package that fits you.
If I'm not able to travel, can I cancel my Jackson Park Highlands travel package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or amend your Jackson Park Highlands travel package for free if you’ve booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your hotel, car rental company or airline may impose a fee. Looking for more information? Have a look at 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 Jackson Park Highlands?
If you love getting an amazing deal, bundle your bookings into a Jackson Park Highlands travel package. Whether you’re looking for hotels, flights, rental cars or activities, you can browse and book them all in one place. You’ll have endless choice at your fingertips too. Expedia has more than 550 partner airlines and 1,000,000 hotels around the globe to choose from. Fly with who you prefer, find a room where you like and save your hard-earned money — now that’s the perfect holiday!
Does Expedia offer Book Now, Pay Later Jackson Park Highlands holidays?
Good news! We do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply pick the payment plan that suits you best during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna’s manageable monthly instalment plans. If making small repayments each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you’d like to pay for your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you spot an amazing deal but don’t have the full amount yet, Klarna’s low deposit holiday plan will help you lock in your getaway.

Where should I stay in Jackson Park Highlands?
A trip to Jackson Park Highlands isn’t over until you’ve seen Millennium Park and Wrigley Field. Stay as close as possible for quick access to these famous tourist attractions.
What are the top hotels in Jackson Park Highlands?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most popular properties in Jackson Park Highlands. Why not have a look at the facilities and rates at each and then make a decision?
How far in advance should I book my Jackson Park Highlands holiday?
To land discount prices, book early. Air carriers typically release flight tickets, along with some of the lowest fares, up to a year ahead of time. Hotels, activities and car rental should also be booked early to avoid disappointment. If you’re in need of a last-minute getaway to Jackson Park Highlands, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Jackson Park Highlands travel package include?
Expedia has all you need to organise your Jackson Park Highlands escape, but what goes into your package is your call. Choose from any combination of hotels, rental cars and flights. In search of some tours or activities to fill in your time? Once you’ve made your booking, you can add them on too. Whatever your budget, there’s a package deal to match your needs.
What should I know before booking a Jackson Park Highlands travel package?
Bundling your bookings into a Jackson Park Highlands travel package is the easiest way to organise your trip. Not only that, you’ll get great discounts when you combine your hotels, flights and car rentals. Once you’ve booked, why not add on a tour or an activity?
Can I choose my airline with a Jackson Park Highlands Expedia travel package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply select the airline you want and craft your ideal Jackson Park Highlands trip.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier

Things to do

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

£43
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

£17
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
See all activities in Chicago

More trip options

* 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.