Roseland Holidays from £978

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,503, price is now £978 per person
£978
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Rooms were small, but for the price it was good. The valet was expensive and took a while to get our car, but I don't think they are associated with the hotel, just use their lobby.

Reviewed on 3 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was £1,477, price is now £1,001 per person
£1,001
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I love the pool and exercise room access, breakfast was amazing

Reviewed on 1 Jul 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £1,544, price is now £1,118 per person
£1,118
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
O

Reviewed on 1 Jul 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 £2,715, price is now £1,994 per person
£1,994
per person
22 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.

Reviewed on 3 Jul 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was £1,522, price is now £1,125 per person
£1,125
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Everything was lovely, but for reference the rooms with views on the first 5-6 floors are extremely noisy at night due to traffic etc.. Not the properties fault, although I would have thought there might be noise canceling glass or something like other hotels I've stayed at.

Reviewed on 30 Jun 2026

Where to stay in Roseland

Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
A busy city street with tall buildings, a bus, and cars.

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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £128 per night from 6 Jul to 7 Jul
£128
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very good! (1,684 reviews)
"Absolutely wonderful experience staying here beautiful view of the city. Complimentary breakfast was wonderful and extremely friendly and helpful staff. Highly recommend staying here"

Reviewed on 3 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 £108 per night from 6 Jul to 7 Jul
£108
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,145 reviews)
"We got in pretty late. The front desk staff that assisted us barely put more than 5 words together. He didn’t give any information..most of all the things that didn’t work/broken. The room was extremely small, the bathroom so tight if you closed the door while on the toilet your knees would be jammed ..."

Reviewed on 3 Jul 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is £161 per night from 6 Jul to 7 Jul
£161
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,842 reviews)
"The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!"

Reviewed on 3 Jul 2026

Omni Chicago Hotel
See all 4,196 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 £978, 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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 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.