Streeterville Holidays from £809

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Streeterville Holiday

If you're wanting a lakeside escape, our Streeterville holiday packages are what you need. Whether you want to experience its families, history or culture, this neighbourhood has a little bit of something for everyone. Some leading nearby attractions to see during your trip to Streeterville include Millennium Park, Willis Tower and Art Institute of Chicago. Stop dreaming and start doing. When you're ready to book your holiday to Streeterville, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was £1,039, price is now £809 per person
£809
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Room was clean but the soap dispenser at the sync and in shower were not working as it supposed to.

Reviewed on 5 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,124, price is now £819 per person
£819
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Love the room! Very ritzy!!

Reviewed on 8 Feb 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was £1,566, price is now £1,180 per person
£1,180
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Gorgeous property, facilities, and location.

Reviewed on 6 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,099, price is now £837 per person
£837
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on 2 Feb 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,159, price is now £886 per person
£886
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on 31 Jan 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 featuring 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

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 £115 per night from 11 Feb to 12 Feb
£115
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (3,281 reviews)
Nice

Reviewed on 2 Feb 2026

Hotel Riu Plaza Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Fully refundableReserve now, pay when you stay
The price is £73 per night from 22 Feb to 23 Feb
£73
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (3,058 reviews)
it was good

Reviewed on 3 Feb 2026

Aloft Chicago Mag Mile
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 £91 per night from 16 Feb to 17 Feb
£91
16 Feb - 17 Feb
includes taxes & fees
8.8/10 Excellent! (3,782 reviews)
Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!

Reviewed on 4 Feb 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,785 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Streeterville travel package cost?
From as little as £809. Yes, you read that correctly. Our Streeterville packages are the quickest way to stretch your budget further. Combine your preferred flights, hotels and rental car and discover this popular destination.
If I'm not able to travel, can I cancel my Streeterville travel package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Streeterville travel package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may be charged a fee by your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Streeterville?
Booking a Streeterville travel package with Expedia is such a simple way to save. We offer access to over 550 partner airlines and 1,000,000 hotel options spread across the globe. With such a fabulous range to pick from, you'll have no difficulty putting together your next dream getaway.
Does Expedia offer Book Now, Pay Later Streeterville holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you stumble on an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Streeterville?
Visitors come from all over the world to experience Millennium Park and Wrigley Field in Streeterville. Stay close to these fantastic attractions and visit them whenever you want.
What are the top hotels in Streeterville?
Make a reservation at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another highly rated option in Streeterville is The Godfrey Hotel Chicago.
How far in advance should I book my Streeterville holiday?
It's difficult to pick the ideal time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available up to 12 months in advance. If you can't book early, fear not. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Streeterville travel package include?
Much of that depends on you. You can pick from a range of Streeterville bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your ideal Streeterville trip looks like, get ready to save!
What should I know before booking a Streeterville travel package?
When you book your flights, hotels and car rentals together, you'll land great discounts. Whether you're planning a beach break in a villa or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Streeterville Expedia travel package?
You can. Expedia has access to more than 550 partner airlines around the world, so fly with the carrier that matches your needs.

Popular places to visit

John Hancock Center featuring a city, night scenes and landscape views

875 North Michigan Avenue

4.5/5(84 reviews)

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

875 North Michigan Avenue

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
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. Flight-inclusive packages are ATOL protected.