Streeterville Vacations from ￥214,261

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The Latest Streeterville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥277,320, price is now ￥214,261 per person
￥214,261
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.

Reviewed on Aug 20, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥316,742, price is now ￥222,542 per person
￥222,542
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Great experience, highly recommended.

Reviewed on Aug 21, 2025

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was ￥659,695, price is now ￥502,288 per person
￥502,288
per person
Oct 9 - Oct 14
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (884 reviews)
Good stay at the Sentral. Our apartment was spacious and it was very convenient to the Art Institute, Field Museum, Shedd Aquarium and Millennium Park.

Reviewed on Aug 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥557,284, price is now ￥435,288 per person
￥435,288
per person
Oct 12 - Oct 16
found 19 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was ￥584,104, price is now ￥457,984 per person
￥457,984
per person
Oct 12 - Oct 16
found 19 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug 10, 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 ￥22,256 per night from Sep 2 to Sep 3
￥22,256
￥26,127 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 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 ￥23,414 per night from Aug 24 to Aug 25
￥23,414
￥27,488 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,666 reviews)
"What i liked was its location. In the middle of everything. But off the busy street. Restaurants & shopping a block away. What needs to be done is an upgrade to the bathroom. Wasn't bad , but tub/shower area need some attention."

Reviewed on Aug 20, 2025

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 ￥16,985 per night from Sep 2 to Sep 3
￥16,985
￥19,939 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (3,524 reviews)
"I love this property even tho it has no “frills.” I will stay at the Whitehall each time I come to Chicago. It’s in a wonderful, safe neighborhood and is one block away from Starbucks, although It is surrounded by high end restaurants and stores. Transportation in all forms are close by. To me, although ..."

Reviewed on Aug 21, 2025

The Whitehall Hotel, BW Premier Collection
See all 4,587 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 ￥214,261, 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

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

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

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.