Roseland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Reception
    Aug 2 - Aug 7

    Hilton Garden Inn Naperville/Warrenville + Flight

    Warrenville
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "-"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,084
    CA $757
    per traveller
    found 1 day ago
    Hilton Garden Inn Naperville/Warrenville
  • Full-size fridge, microwave, oven, stovetop
    Aug 2 - Aug 7

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,307
    CA $1,531
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Indoor wedding
    Jun 30 - Jul 3

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,349 reviews)
    "It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,145
    CA $782
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Seasonal outdoor pool, sun loungers
    Aug 2 - Aug 7

    Viceroy Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,230 reviews)
    "I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,510
    CA $1,752
    per traveller
    found 1 day ago
    Viceroy Chicago
  • Terrace/patio
    Jun 30 - Jul 3

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "The view from our room was awesome!!"
    Reviewed May 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,024
    CA $1,420
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

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

Roseland Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is CA $281 per night from Jun 3 to Jun 4
CA $281
CA $334 total
Jun 3 - Jun 4
includes taxes & fees
8/10 Very Good! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on May 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,263 reviews)
"The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent. My wife and I stayed in that place for eight days and seven nights and ..."

Reviewed on May 27, 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
The price is CA $263 per night from Jun 21 to Jun 22
CA $263
CA $312 total
Jun 21 - Jun 22
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"Everything"

Reviewed on May 27, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,402 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Roseland vacation 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 vacation 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 vacation 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 vacation 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 fulfill those vacation 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 Center, Abbott Park and Bronzeville Childrens Museum are some top ones to add to your itinerary.
How far in advance should I book my Roseland vacation?
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 traveling 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 vacation is just clicks away.
Can I choose my airline with a Roseland Expedia vacation 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 vacation package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or change your Roseland vacation 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

Wrigley Field

Wrigley Field

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

Wrigley Field
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
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

You can enjoy some retail therapy 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

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
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.