Streeterville Holidays

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Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 21 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Overall great experience. No complaints!!!

Reviewed on 22 Apr 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 21 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean.

Reviewed on 22 Apr 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 23 hours ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Great breakfast every morning, the staff does a great job of making sure you enjoy the start of each day. Very walkable, its close proximity to Michigan Ave makes a trip to Chicago without a vehicle totally doable. We will be back - thank you for the great place to stay and enjoy a vacation in Chicago!

Reviewed on 24 Apr 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 23 hours ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
The highlight of this hotel is definitely the staff — everyone was kind, professional, and very helpful throughout our stay. Unfortunately, we did experience an issue with housekeeping, as our room wasn’t cleaned for two days. However, when I brought it to the attention of the front desk, they promptly addressed the situation and kindly removed our bar charges, which was very much appreciated. The hotel bar is one of the main attractions and definitely worth checking out!

Reviewed on 22 Apr 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 featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Streeterville

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 HK$1,279 per night from 11 May to 12 May
HK$1,279
HK$1,501 total
includes taxes & fees
11 May - 12 May
"Nice"

Reviewed on 22 Apr 2025

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 HK$1,125 per night from 30 Apr to 1 May
HK$1,125
HK$1,540 total
includes taxes & fees
30 Apr - 1 May
9.2/10 Wonderful! (1,744 reviews)
Best hotel
"Great stay"

Reviewed on 21 Apr 2025

Hotel Riu Plaza Chicago
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile
3 out of 5
165 East Ontario Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is HK$1,088 per night from 1 May to 2 May
HK$1,088
HK$1,278 total
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (1,319 reviews)
"Elevators needing room keys to access is nice"

Reviewed on 22 Apr 2025

Courtyard by Marriott Chicago Magnificent Mile
See all 4,140 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 HK$4,591, 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 holiday 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 holiday 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 neighbourhood’s most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville holiday?
Travellers 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 holiday rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia holiday 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 holiday.
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.

Popular places to visit

Water Tower Place

Water Tower Place

4/5(24 reviews)

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

Water Tower Place

Prentice Women's Hospital

If Prentice Women's Hospital is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Prentice Women's Hospital

Things to do

Flyover in Chicago

Flyover in Chicago

HK$295
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

HK$378
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

HK$279
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.