Roseland Holidays from £1,136
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Your Roseland Holiday
Take all the hassle out of planning your next adventure with a Roseland holiday package. Immerse yourself in the sights and sounds of this enticing neighbourhood and enjoy what it has to offer. Kick off your trip to Roseland with a visit to nearby attractions such as Harborside International Golf Centre, Abbott Park and Bronzeville Childrens Museum. Whatever your dream Roseland holiday may look like, you can turn it into reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
£1,348
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on 17 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,441
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
There need to be more paper-cup for coffee-machine.
Reviewed on 17 Aug 2026
Where to stay in Roseland
Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
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.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Roseland
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£95
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,248 reviews)
"The hotel is in a great location right across from Grant Park but the hotel is really dated. I usually love a historic hotel… but this one needs a little love. Our room was “ok”… everything worked and we didn’t have any issues but it was just old and felt old. I wouldn’t stay here again. If you do ..."
Reviewed on 18 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
8/10 Very good! (2,029 reviews)
"Very friendly and professional staff. Building does show its age though."
Reviewed on 18 Aug 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (859 reviews)
"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit ..."
Reviewed on 18 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 Roseland travel package cost?
Starting from just £1,136, a package is your gateway to cheap travel. Custom make your Roseland adventure by selecting from our comprehensive range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Roseland travel package?
Yes, it's possible to cancel your Roseland booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Roseland?
Our Roseland travel packages promise plenty of savings for the savvy traveller. For the best deals, simply bundle your hotel, flights and extras (such as activities) into a handy package. But impressive bargains are only the start of your next amazing adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties throughout the world to select from. Whatever your style or budget, there's a travel package to suit you.
Does Expedia offer Book Now, Pay Later Roseland holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Check out these flexible payment options:
- Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying just a small amount each month works for you, pick this option during the checkout process.
- Pay in instalments holidays: If you want to pay for your escape across 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 come across an incredible deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Roseland?
A journey to Roseland isn't over until you've seen Millennium Park and Wrigley Field. Stay nearby and easily access these popular sights.
What are the top hotels in Roseland?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most popular hotels in Roseland. Why not have a look at the facilities and amenities at each and then make up your mind?
How far in advance should I book my Roseland holiday?
It can be tricky to know when is the ideal time to book your Roseland holiday. But usually the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels nearly 12 months prior to departure. If you're thinking of a last-minute getaway, no need to fret! There are terrific bargains announced on Expedia every single day.
What does an Expedia Roseland travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your dream Roseland getaway. You can also add on fun stuff like activities and tours once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll enjoy deals you won't find elsewhere.
What should I know before booking a Roseland travel package?
When you book your flights, hotels and car rentals together, you'll score amazing discounts. Whether you're organising a wilderness getaway in a cabin or would rather stay in a convenient hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Roseland Expedia travel package?
Yes — that's the beauty of an Expedia travel package. You're in control. We have access to more than 550 partner airlines throughout the world, so you have lots of choice when planning your Roseland adventure.
Stay near popular Roseland attractions
Abbott Park
Abbott Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Chicago State University
Explore the campus of Chicago State University as part of your travels around Chicago. Amble around the area's parks or visit its shops.
Jones Convocation Center
Catch an event at Jones Convocation Center during your trip to Chicago. Amble around the area's parks or visit its shops.
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.