Roseland Holidays from £1,006

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Friendly bartender made the whole trip amazing, the beds and bathroom were really nice!

Reviewed on 22 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Property location was perfect! Rooftop top views was amazing!

Reviewed on 23 Jun 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (1,833 reviews)
The Hotel is physically beautiful. The rooms are spacious and comfortable in general. The food is good. We did not appreciated at all the waiting time to get the room. Check in was at 3:00pm, but the room was not available and hsd to wait for so long after a long traveling day... That's a no,.. no. The breakfast took very long time with only a couple of tables occupied however it was good.

Reviewed on 23 Jun 2025

Where to stay in Roseland

Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
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 Roseland

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 £132 per night from 1 Jul to 2 Jul
£132
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (4,265 reviews)
"Great location, we enjoyed our stay"

Reviewed on 23 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £160 per night from 1 Jul to 2 Jul
£160
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,918 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on 24 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
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 £117 per night from 6 Jul to 7 Jul
£117
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,334 reviews)
"The best value in Chicago.The staff is gracious and accommodating, the restaurant is an amazingly suprising, and a find at fair prices. Hidden away with easy access to the shoreline. At the doorstep of the Gold Coast without the hubbub."

Reviewed on 23 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,179 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 £1,006, 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

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
Navy Pier

Navy Pier

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

Navy Pier
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

Things to do

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
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
92% 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.