Roseland Holidays from £916

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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,176, price is now £916 per person
£916
per person
22 May - 25 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Everything was perfect

Reviewed on 26 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,299, price is now £984 per person
£984
per person
22 May - 25 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though.

Reviewed on 2 Apr 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,431, price is now £1,093 per person
£1,093
per person
22 May - 25 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.

Reviewed on 2 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,558, price is now £1,218 per person
£1,218
per person
22 May - 25 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on 31 Mar 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was £1,536, price is now £1,230 per person
£1,230
per person
22 May - 25 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great location and property

Reviewed on 14 Mar 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

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 Roseland

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 £96 per night from 5 Apr to 6 Apr
£96
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (10,007 reviews)
Good location for where we needed to be in the city. It’s a very dated hotel.

Reviewed on 2 Apr 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 5 Apr to 6 Apr
£115
5 Apr - 6 Apr
includes taxes & fees
9/10 Wonderful! (4,039 reviews)
The toliet was loose in the bathroom

Reviewed on 2 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is £127 per night from 12 Apr to 13 Apr
£127
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (5,810 reviews)
Not clean, worn off properly

Reviewed on 3 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,414 properties in Roseland
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 Roseland travel package cost?
Starting from just £916, 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.

Popular places to visit

Magnificent Mile

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Magnificent Mile
Downtown Chicago

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Downtown Chicago
Wrigley Field

Wrigley Field

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

Wrigley Field

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£82
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.