Streeterville Holidays

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    Save up to €185 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
8 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,988 reviews)
Wonderful! Exceptional! The rooms

Reviewed on 1 Apr 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
8 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Nice swimming pool for lap swimming.

Reviewed on 23 Mar 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
8 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Great location and beautiful hotel. However- room amenities were missing basic needs like iron, ironing boards, slippers, full length mirror and no working desk. Not good for business needs at all.

Reviewed on 1 Apr 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
8 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Enjoyed our stay!! Rooms were clean and breakfast was top tier with many options. They don’t have valet, but they do have self pay parking across the street for $55 a day. Front desk staff professional and helpful.

Reviewed on 1 Apr 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
8 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
What an amazing experience we had at The Emily. From their stylish coffee shop to their upscale dining experience, this is the place to stay if you are just visiting or looking for an escape from the 9 to 5. The local restaurants are absolute gems, and entertainment can be found in any direction. I’m booking my next stay now, can’t wait to be back in summer!

Reviewed on 30 Mar 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

5 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 €128 per night from 21 Apr to 22 Apr
€128
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (2,088 reviews)
Great location!
"My family stayed here over spring break. Checkin was fast and seamless. The bellman met us at the car and took our bags up to our room. The staff was helpful during our stay. Everyone was friendly. Front desk was helpful. The bar/restaurant closed for a few days, but the front desk gave us bottled ..."

Reviewed on 31 Mar 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 €144 per night from 6 Apr to 7 Apr
€144
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (1,495 reviews)
"lovely property with friendly staff"

Reviewed on 30 Mar 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 €120 per night from 6 Apr to 7 Apr
€120
includes taxes & fees
6 Apr - 7 Apr
8.8/10 Excellent! (1,269 reviews)
"Staff was very helpful"

Reviewed on 29 Mar 2025

Courtyard by Marriott Chicago Magnificent Mile
See all 4,120 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 holiday package cost?
Maybe less than you might think — from as low as €660, in fact! By bundling hotels, flights and car rentals into a custom-built holiday 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 holiday package?
Yes you can, and we’re here to help. You may be able to cancel or amend your Streeterville holiday 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
John Hancock Center

John Hancock Center

4.5/5(84 reviews)

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

John Hancock Center
The Loop - Downtown

Wrigley Building

4.5/5(3 reviews)

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Wrigley Building

Things to do

Flyover in Chicago

Flyover in Chicago

€35
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

€45
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€20
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.