Streeterville Vacations from ￥314,217

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Streeterville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥374,696, price is now ￥314,217 per person
￥314,217
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great weekend getaway with a beautiful view!

Reviewed on Mar 29, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥546,288, price is now ￥399,292 per person
￥399,292
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The service is always outstanding! Especially Adrian! I have gotten to know him over the last few stays and his smile is infectious. You are so lucky to have this guy.

Reviewed on Mar 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Elegant and beautiful

Reviewed on Mar 26, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥446,148, price is now ￥381,583 per person
￥381,583
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
This was perfect for a night in the city! Great all around and will stay again. Great staff at check-in!

Reviewed on Mar 27, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥443,372, price is now ￥382,310 per person
￥382,310
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Great room and staff

Reviewed on Mar 28, 2026

Where to stay in Streeterville

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

Streeterville Hotel Deals

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 ￥19,587 per night from Apr 12 to Apr 13
￥19,587
￥22,993 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,007 reviews)
Nice location and awesome room

Reviewed on Mar 29, 2026

Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,680 per night from Apr 5 to Apr 6
￥20,680
￥28,795 total
Apr 5 - Apr 6
includes taxes & fees
9.4/10 Exceptional! (3,659 reviews)
The service is always outstanding! Especially Adrian! I have gotten to know him over the last few stays and his smile is infectious. You are so lucky to have this guy.

Reviewed on Mar 29, 2026

Hotel Riu Plaza Chicago
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 ￥27,092 per night from Apr 27 to Apr 28
￥27,092
￥31,807 total
Apr 27 - Apr 28
includes taxes & fees
8.4/10 Very Good! (1,759 reviews)
No microwave in the room, had to pay for wifi, pool was smaller then expected. Didn't have a wow experience 😕

Reviewed on Mar 29, 2026

The Wade
See all 4,597 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 ￥314,217, 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

875 North Michigan Avenue

875 North Michigan Avenue

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.

875 North Michigan Avenue
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
Chicago Children's Museum

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 theater scene.

Chicago Children's Museum

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,829
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of 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.