Streeterville Vacations from ￥766,017

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    Save up to ￥109,000 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.
Central Loop Hotel

Central Loop Hotel

4 out of 5
Downtown Chicago
Price was ￥1,078,045, price is now ￥766,017 per person
￥766,017
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,333 reviews)
Property is very nice and well managed, it’s an older space but upkeep is very good. Felt safe as a solo traveller with room card access to room floors

Reviewed on Nov 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥1,202,076, price is now ￥825,195 per person
￥825,195
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here

Reviewed on Nov 4, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥1,190,058, price is now ￥839,533 per person
￥839,533
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Staff was friendly and the room was clean

Reviewed on Nov 3, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥1,096,067, price is now ￥776,296 per person
￥776,296
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)

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 ￥1,184,298, price is now ￥841,185 per person
￥841,185
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
A busy city street with tall buildings, a bus, and cars.

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

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 ￥18,860 per night from Nov 23 to Nov 24
￥18,860
￥22,422 total
Nov 23 - Nov 24
includes taxes & fees
8.6/10 Excellent! (2,185 reviews)
"Great Hotel, Amazing Views, but Some Nighttime Noise We had a wonderful stay at The Wade Hotel in Chicago! The location was excellent, the rooms were very clean and comfortable, and the views were absolutely beautiful, definitely one of the highlights of our stay. The only downside was a constant ..."

Reviewed on Nov 4, 2026

The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,480 per night from Nov 11 to Nov 12
￥16,480
￥19,592 total
Nov 11 - Nov 12
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
162 East Ontario Street Chicago IL
The price is ￥14,158 per night from Nov 22 to Nov 23
￥14,158
￥17,115 total
Nov 22 - Nov 23
includes taxes & fees
Hotel Saint Clair- Magnificent Mile
See all 4,609 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 ￥766,017, 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.

Stay near popular Streeterville attractions

A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

Water Tower Place

9.0/10 (1,113 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,809
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,269
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,636
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.