Roscoe Village Vacations from ￥332,300

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The Latest Roscoe Village Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥399,876, price is now ￥332,300 per person
￥332,300
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Patrick was excellent at check in despite how busy it was. I felt the staff handled the crush of people efficiently and pleasantly. I was pleasantly surprised I received $15 per day towards the bar or snack room. The snack room selections included hot and cold items. My room was a bit hot for my taste and they took care of it immediately.

Reviewed on May 3, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ￥445,300, price is now ￥365,962 per person
￥365,962
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥406,322, price is now ￥337,637 per person
￥337,637
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on May 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥417,582, price is now ￥347,248 per person
￥347,248
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥399,074, price is now ￥332,308 per person
￥332,308
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌

Reviewed on May 7, 2026

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

Downtown Chicago

4 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

Roscoe Village Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,551 per night from May 20 to May 21
￥13,551
￥20,901 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (2,694 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on May 8, 2026

Hotel Felix River North/Magnificent Mile
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 ￥20,955 per night from May 10 to May 11
￥20,955
￥24,916 total
May 10 - May 11
includes taxes & fees
8/10 Very Good! (10,188 reviews)
Room was clean, coffee maker didn’t work but was replaced quickly. Staff all very helpful, especially Steve the doorman/security. Very helpful getting us a cab!

Reviewed on May 8, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,507 per night from May 25 to May 26
￥22,507
￥26,758 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,185 reviews)
Get the breakfast, you go next door with coupons and it’s excellent! So convenient. We also went there for drinks and appetizers before going to the Chicago theater.

Reviewed on May 8, 2026

River Hotel
See all 4,732 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 vacation package cost?
Our Roscoe Village packages, which start from as low as ￥332,300, are the easiest way to save money. Select your favorite 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 vacation 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 vacation?
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 vacation 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 vacation 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 vacation.
If I'm not able to travel, can I cancel my Roscoe Village vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.