Streeterville Vacations from ￥334,457

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The Latest Streeterville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥392,662, price is now ￥334,457 per person
￥334,457
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
We really enjoyed our stay. The staff was super friendly!

Reviewed on Sep 1, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥513,846, price is now ￥405,233 per person
￥405,233
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
The property was absolutely beautiful and the staff was amazing

Reviewed on Sep 1, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥470,333, price is now ￥380,461 per person
￥380,461
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥401,175, price is now ￥341,653 per person
￥341,653
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Fantastic hotel at the Mag Mile area. New, clean, safe, friendly staff. Very walkable and safe area. For those who need parking, the iParkit facility in St. Clair st is right across the street. I loved my time here.

Reviewed on Sep 1, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥400,948, price is now ￥342,372 per person
￥342,372
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back!

Reviewed on Aug 31, 2025

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago showing 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

Streeterville Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥24,557 per night from Sep 22 to Sep 23
￥24,557
￥28,826 total
Sep 22 - Sep 23
includes taxes & fees
8.2/10 Very Good! (1,156 reviews)
"I enjoyed the location"

Reviewed on Aug 29, 2025

The Wade
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 ￥23,624 per night from Sep 22 to Sep 23
￥23,624
￥27,732 total
Sep 22 - Sep 23
includes taxes & fees
Hilton Chicago/Magnificent Mile Suites
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,579 per night from Sep 2 to Sep 3
￥17,579
￥20,638 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (3,409 reviews)
"Great location but breakfast is poor."

Reviewed on Aug 30, 2025

The Whitehall Hotel, BW Premier Collection
See all 4,666 properties in Streeterville
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 Streeterville vacation package cost?
Maybe less than you might think — from as low as ￥334,457, in fact! By bundling hotels, flights and car rentals into a custom-built vacation package, your Streeterville escape is just clicks away.
How do I get a cheap travel package to Streeterville?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Streeterville vacation package. You won't just pick up amazing discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 hotels throughout the world. Your dream vacation starts right here, right now!
Where should I stay in Streeterville?
Most people who travel to Streeterville include both McCormick Place and Millennium Park on their must-see lists. Why not reserve a hotel near these main attractions?
What are the top hotels in Streeterville?
Make a reservation at Sable at Navy Pier Chicago, Curio Collection by Hilton. It's one of the neighborhood's most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville vacation?
Travelers are usually able to browse international flights on Expedia up to 12 months prior to departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Streeterville travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to crafting your Streeterville getaway, you're in charge!
What should I know before booking a Streeterville travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Bundle your car rentals, airfares and hotels into a neat package. But you're not restricted to hotels. Expedia offers all sorts of properties, including vacation rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select the carrier you want and create your ideal Streeterville vacation.
If I'm not able to travel, can I cancel my Streeterville vacation package?
Yes you can, and we're here to help. You may be able to cancel or amend your Streeterville vacation package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for more information.

Discover the most popular places to visit in Streeterville

Water Tower Place

Water Tower Place

4.5/5(834 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
John Hancock Center featuring a city, night scenes and landscape views

John Hancock Center

4.5/5(1,913 reviews)

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

John Hancock Center
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Chicago Children's Museum

4.5/5(196 reviews)

You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Chicago Children's Museum

Things to do

River tour boat in Chicago

Architecture River Tour

￥6,127
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

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

￥6,208
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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.