Roseland Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Roseland Holiday

Our Roseland holiday packages are a simple and practical way to plan and book your next break. Discover the heart and soul of this unique neighbourhood without the bother of planning everything yourself. Begin your trip to Roseland with a visit to nearby attractions such as Abbott Park, Harborside International Golf Centre and A. Philip Randolph Pullman Porter Museum. Expedia will help put your travel plans into action. Book your ultimate Roseland holiday now.

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

    Omni Chicago Hotel + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$991
    AU$739
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Serves breakfast, lunch and dinner
    Aug 14 - Aug 16

    JW Marriott Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."
    Reviewed May 31, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,110
    AU$806
    per traveller
    found 1 day ago
    JW Marriott Chicago
  • Premium bedding, pillow-top beds, in-room safe, individually furnished
    Aug 14 - Aug 16

    Level Chicago - River North + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,012 reviews)
    "I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,094
    AU$825
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Terrace/patio
    Aug 14 - Aug 16

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    2 nights
    5.0 star property
    9.6/10 - Exceptional (1,878 reviews)
    "Great room, professional staff, no complaints."
    Reviewed May 31, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    AU$1,591
    AU$1,200
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Lobby
    Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,750 reviews)
    "Hotel staff was super nice. Great location to be in walking distance of a lot of places."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,034
    AU$781
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile

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
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

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 AU$231 per night from 29 June to 30 June
AU$231
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,166 reviews)
"Apparently it's haunted and I had the room across the hall from the haunted room. I didn't know this until my third night there, but it was quiet and calm."

Reviewed on 4 June 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is AU$253 per night from 28 June to 29 June
AU$253
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,510 reviews)
"Clean room"

Reviewed on 3 June 2026

The Chicago Hotel Collection - Magnificent Mile
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 AU$355 per night from 30 June to 1 July
AU$355
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,331 reviews)
"Urine in toilet upon entering, garbage left in room , rooftop glass floor closed not mentioned"

Reviewed on 4 June 2026

Hotel Riu Plaza Chicago
See all 4,378 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$56
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.