Roscoe Village Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Where to stay in Roscoe Village

Find the best Roscoe Village areas and neighborhoods for the activities you enjoy most. Learn more about Roscoe Village
Downtown Chicago which includes 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 Roscoe Village

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 S$267 per night from 4 Aug to 5 Aug
S$267
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (9,011 reviews)
"2 issues # toilet lever hard to push #2 door restroom hard to open other than that everything else was fine."

Reviewed on 28 Jul, 2025

Congress Plaza Hotel
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 S$408 per night from 22 Aug to 23 Aug
S$408
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (2,112 reviews)
"Great experience!"

Reviewed on 25 Jul, 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 S$216 per night from 17 Aug to 18 Aug
S$216
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,529 reviews)
"Convenient to the public transportation and nearby shopping. On-site restaurant was a good breakfast option for us before heading out for the day."

Reviewed on 24 Jul, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,682 properties in Roscoe Village
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 Roscoe Village holiday package cost?
Our Roscoe Village packages, which start from as low as , are the easiest way to save money. Select your favourite hotels, flights and more to create your perfect getaway.
How do I get a cheap travel package to Roscoe Village?
You'll save a ton of money if you combine your hotels, car rentals and flights into a Roscoe Village holiday package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 properties all over the world, so you'll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Roscoe Village?
Urban explorers come from all corners of the globe to experience Wrigley Field and Lincoln Park Zoo in Roscoe Village. Book a room near these must-see attractions and visit them at your leisure.
How far in advance should I book my Roscoe Village holiday?
The earlier, the better. Air carriers generally release flights up to a year ahead of departure, and this is a great opportunity to score some of the cheapest prices. Just been told you should take some holiday time in a few weeks? No sweat. Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Roscoe Village travel package include?
Hotels, flights and rental cars — we've got them well covered. With Expedia, you can create your Roscoe Village package however you want. All you have to do is work out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the more you save!
What should I know before booking a Roscoe Village travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and score fabulous discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside villas, mountain cabins and even glamping tents!
Can I choose my airline with a Roscoe Village Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply choose the carrier you want and craft your ideal Roscoe Village holiday.
If I'm not able to travel, can I cancel my Roscoe Village holiday package?
Yes, it's possible to cancel your Roscoe Village booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
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

S$58
per adult
94% 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.