Jackson Park Highlands Holidays from £1,436

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,131, price is now £1,436 per person
£1,436
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on 13 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,103, price is now £1,493 per person
£1,493
per person
14 Jun - 21 Jun
found 1 day 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

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 £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,556, price is now £1,845 per person
£1,845
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location. Very friendly and helpful staff.

Reviewed on 13 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,010, price is now £2,205 per person
£2,205
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!

Reviewed on 13 May 2026

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

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 Jackson Park Highlands

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is £117 per night from 26 May to 27 May
£117
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,224 reviews)
Great service and staff

Reviewed on 13 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £145 per night from 25 May to 26 May
£145
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,135 reviews)
The property, our room, and the staff were all FIVE STARS! Highly recommend this place!!

Reviewed on 13 May 2026

Hotel Riu Plaza Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £126 per night from 25 May to 26 May
£126
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,164 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on 11 May 2026

River Hotel
See all 4,337 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
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Family Friendly Holidays

Frequently asked questions

How much does a Jackson Park Highlands travel package cost?
The cheapest Jackson Park Highlands travel package is £1,436, 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

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
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% 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
Flyover in Chicago

Flyover in Chicago

£16
per child
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.