Roseland Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Aug 14 - Aug 16

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Great day super nice staff and very helpful comfortable clean, and a great location at a reasonable price very pleased"
    Reviewed May 20, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$999
    NZ$787
    per traveller
    found 4 hours ago
    Le Méridien Essex Chicago
  • Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,715 reviews)
    "A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,164
    NZ$878
    per traveller
    found 4 hours ago
    Hotel Felix River North/Magnificent Mile
  • Aug 14 - Aug 16

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,164 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,127
    NZ$859
    per traveller
    found 4 hours ago
    Fairmont Chicago at Millennium Park
  • Aug 14 - Aug 16

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.6/10 - Exceptional (4,075 reviews)
    "The property has a very convenient location. The room is spacious. They offer free but good coffee and popcorn at the lobby every day. And the cold water from the tab is filtered. Definitely will come back."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,106
    NZ$885
    per traveller
    found 4 hours ago
    L7 Chicago by LOTTE
  • Aug 14 - Aug 16

    Swissotel - Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.0/10 - Wonderful (3,336 reviews)
    "Great location and very convenient to river walk and vicinity."
    Reviewed May 22, 2026
    Return New York (LGA) - Chicago (ORD)
    LGA - ORDDirect ORD - JFKDirect
    NZ$1,201
    NZ$964
    per traveller
    found 4 hours ago
    Swissotel - Chicago

Our guide on where to stay in Roseland

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

Our pick of the best Roseland Hotel Deals

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 NZ$271 per night from 25 May to 26 May
NZ$271
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,131 reviews)
"Did not have hot water when we returned to room after concert. Next morning called and maintenance came to fix. Good location to walk to South Shore train station and Grant Park"

Reviewed on 23 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 NZ$372 per night from 27 May to 28 May
NZ$372
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,213 reviews)
"Very clean, staff is helpful, curious & so polite. I will be staying there anytime I visit Chicago. Location is ideal being located right off Michigan Ave.. Best breakfast buffet. Rooftop restaurant was Amazing! 100 stars if I could!"

Reviewed on 23 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 NZ$247 per night from 25 May to 26 May
NZ$247
25 May - 26 May
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
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 holiday package cost?
Get set to book, because a getaway to Roseland starts from just . When you combine your hotels, flights and car rentals into a holiday package, you'll score the best deals.
How do I get a cheap travel package to Roseland?
Simply by bundling. Hotels, rental cars and flights — combine whatever you need into a Roseland holiday package and save. Score even more bargains when you include extras such as tours or experiences to your booking. But that's not the only impressive part. You have the freedom to put together your holiday your way. We offer more than 550 partner airlines and 1 000 000 hotel options throughout the world, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Where should I stay in Roseland?
With lots to explore in Roseland, it makes sense to lock in a hotel close to its attractions. Harborside International Golf Centre, Abbott Park and Bronzeville Childrens Museum are some top ones to add to your itinerary.
How far in advance should I book my Roseland holiday?
While not all air carriers advertise tickets early, you can usually look up international flights on Expedia up to a year in advance. This is the time when you can bag some fantastic deals. If you're purchasing tickets last minute, you might still get lucky. Low prices occasionally emerge only weeks prior to departure.
What does an Expedia Roseland travel package include?
That depends on what you're after. If you're travelling alone, you might decide to combine hotels and flights. Bringing the whole crew to Roseland? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Roseland travel package?
Discover deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we've got them all. You'll save big dollars just for bundling your bookings. Whether you're going on a ski adventure or sunning yourself on a warm beach, your dream holiday is just clicks away.
Can I choose my airline with a Roseland Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners throughout the world, so you have options galore when arranging your Roseland escape.
If I'm not able to travel, can I cancel my Roseland holiday package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or change your Roseland holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Want more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Roseland

Activities

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.