Jackson Park Highlands Holidays from £475

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £800, price is now £475 per person
£475
per person
13 Nov - 18 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £889, price is now £573 per person
£573
per person
13 Nov - 18 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was £762, price is now £497 per person
£497
per person
13 Nov - 18 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Wonderful staff! Convenient location for walking to restaurants, shopping and right next to a subway station

Reviewed on 30 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,009, price is now £662 per person
£662
per person
13 Nov - 18 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Very impressive, 5 star quality for 4 star prices. Highly recommend.

Reviewed on 30 Aug 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was £852, price is now £566 per person
£566
per person
13 Nov - 18 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on 25 Aug 2025

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

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
Fully refundableReserve now, pay when you stay
The price is £123 per night from 1 Sept to 2 Sept
£123
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on 26 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is £146 per night from 3 Sept to 4 Sept
£146
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on 27 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is £135 per night from 2 Sept to 3 Sept
£135
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,778 reviews)
"Hotel room had the best view of the city"

Reviewed on 27 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,428 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 £475, 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 featuring a city, a sporting event and city views

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

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
Navy Pier

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
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 Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.