Streeterville Holidays from £1,014

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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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

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 £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 23 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
it is great for the pier

Reviewed on 26 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 23 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 23 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great property. Clean and convenient. Only unsightly thing is that there was a dirty t shirt laying in the hallway that nobody seemed to pick up.

Reviewed on 26 Aug 2025

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,907, price is now £1,267 per person
£1,267
per person
8 Oct - 15 Oct
found 23 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,011 reviews)
Bed was comfortable, breakfast good, room VERY small

Reviewed on 24 Aug 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

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 £132 per night from 1 Sept to 2 Sept
£132
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,219 reviews)
"Friendly"

Reviewed on 24 Aug 2025

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 £139 per night from 22 Sept to 23 Sept
£139
22 Sept - 23 Sept
includes taxes & fees
8.8/10 Excellent! (2,701 reviews)
"Good Hotell"

Reviewed on 25 Aug 2025

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 £98 per night from 2 Sept to 3 Sept
£98
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (3,540 reviews)
"I had a great time. We requested a microwave be brought to our room and it was delivered in a few minutes. The breakfast was reaaly nice. We enjoyed walking in the area around the hotel. It was a great stay."

Reviewed on 23 Aug 2025

The Whitehall Hotel, BW Premier Collection
See all 4,587 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
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Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Streeterville travel package cost?
From as little as £1,014. 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

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

Things to do

River tour boat in Chicago

Architecture River Tour

£31
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

£30
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

£31
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. Flight-inclusive packages are ATOL protected.