Roseland Holidays

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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.
  • Smart TV
    Jun 29 - Jul 5

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (480 reviews)
    "Yes"
    Reviewed May 12, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,615
    £1,208
    per traveller
    found 14 hours ago
    Level Chicago Fulton Market
  • Indoor wedding
    Jul 30 - Aug 3

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,331 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    Save 100% on your flight
    £2,783
    £1,819
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,506 reviews)
    "I loved it here and will definitely stay again."
    Reviewed May 18, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,481
    £1,809
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jun 29 - Jul 5

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,875 reviews)
    "Great experience! Would stay here agin"
    Reviewed May 18, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,625
    £1,919
    per traveller
    found 14 hours ago
    Trump International Hotel & Tower Chicago
  • Exterior
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,728 reviews)
    "Great location with a great view. Walking distance to all attractions and restaurants. The room was spacious and comfy beds"
    Reviewed May 18, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,226
    £1,677
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

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 £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,161 reviews)
"It’s old but clean"

Reviewed on 19 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £153 per night from 25 May to 26 May
£153
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,186 reviews)
"My husband and I really enjoyed staying at Hotel Riu Plaza Chicago. Staff was friendly and helpful. Hotel is very clean. Breakfast & bar is so delicious we definitely will come back. Chi Love you! Thank you so much."

Reviewed on 19 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £107 per night from 25 May to 26 May
£107
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,432 reviews)
"Good location, definitely walkable to a lot of shops and restaurants."

Reviewed on 18 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,387 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 , 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

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
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.