Streeterville Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €864, price is now €622 per person
€622
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
The staff from the start were very nice and helpful. The hotel was clean loved the location of the hotel. Will definitely try booking ag this hotel next year

Reviewed on 2 Sep 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €3,218, price is now €2,145 per person
€2,145
per person
5 Nov - 12 Nov
found 2 hours ago
Return direct flight included
Palma de Mallorca (PMI) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!

Reviewed on 2 Sep 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €945, price is now €643 per person
€643
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.

Reviewed on 2 Sep 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,604, price is now €1,781 per person
€1,781
per person
5 Nov - 12 Nov
found 2 hours ago
Return direct flight included
Palma de Mallorca (PMI) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Great hotel, especially for the price, nice area, would go back again if I’m in Chicago.

Reviewed on 2 Sep 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,964, price is now €1,431 per person
€1,431
per person
31 Oct - 3 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Always an amazing place! We keep comi

Reviewed on 2 Sep 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 which includes 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

Top hotels in Streeterville

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 €167 per night from 22 Sept to 23 Sept
€167
22 Sept - 23 Sept
includes taxes & fees
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 €161 per night from 22 Sept to 23 Sept
€161
22 Sept - 23 Sept
includes taxes & fees
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 €120 per night from 4 Sept to 5 Sept
€120
4 Sept - 5 Sept
includes taxes & fees
The Whitehall Hotel, BW Premier Collection
See all 4,666 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 €622, 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 theatre scene.

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 art galleries and notable monuments in this vibrant area.

Wrigley Building

Things to do

River tour boat in Chicago

Architecture River Tour

€36
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

€35
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

€36
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.