Jackson Park Highlands Holidays from £1,234
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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.
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Hotel Felix River North/Magnificent Mile
Downtown Chicago
£1,234
per person
19 Sept - 26 Sept
found 16 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
We visited gor an extended weekend birthday celebration. The hotel was centrally located about 15 minutes walking away from the Magnificent Mile. Restuarants are near by and Walgreens. The staff was very nice and accommodating. A special shout-out to Aldo for his professionalism and helpfulness.
Reviewed on 11 Aug 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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top hotels in Jackson Park Highlands
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£94
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,288 reviews)
"Lower price$"
Reviewed on 11 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
30 Aug - 31 Aug
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
£165
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (2,764 reviews)
"Overall, I’d give my stay about a 3.8/5. There were some good things, but also quite a few areas that could use improvement. The room was really small, and the bathroom felt like it was in a closet — very cramped. The furniture and everything in the room also felt pretty old and worn. The closet ..."
Reviewed on 11 Aug 2026
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.
Frequently asked questions
How much does a Jackson Park Highlands travel package cost?
The cheapest Jackson Park Highlands travel package is £1,234, 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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* 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.