Streeterville Holidays

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    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.
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 5 - Jul 14

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    9 nights
    4.5 star property
    9.4/10 - Exceptional (3,714 reviews)
    "Staff was amazing. The room was cleaned every day. Perfect spot in order to be able to explore throughout the day."
    Reviewed May 20, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £2,031
    £1,482
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Lounge
    Jul 5 - Jul 14

    Pendry Chicago + Flight

    Downtown Chicago
    9 nights
    4.5 star property
    9.2/10 - Wonderful (1,126 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    Save 100% on your flight
    £2,553
    £1,736
    per traveller
    found 1 day ago
    Pendry Chicago
  • Indoor wedding
    Jul 5 - Jul 14

    Swissotel - Chicago + Flight

    Downtown Chicago
    9 nights
    4.5 star property
    9.0/10 - Wonderful (3,334 reviews)
    "Very good Outstanding service "
    Reviewed May 19, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £2,252
    £1,544
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 5 - Jul 14

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    9 nights
    4.0 star property
    9.4/10 - Exceptional (2,508 reviews)
    "The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay."
    Reviewed May 20, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £2,343
    £1,648
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 5 - Jul 14

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    9 nights
    4.5 star property
    8.8/10 - Excellent (2,163 reviews)
    "Great breakfast"
    Reviewed May 20, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £2,266
    £1,626
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago

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 £153 per night from 25 May to 26 May
£153
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,201 reviews)
"Breakfast bar was very good just need 0to go cups for coffee.I'm"

Reviewed on 21 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £107 per night from 25 May to 26 May
£107
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,447 reviews)
"great location and spacious room. good value"

Reviewed on 21 May 2026

The Chicago Hotel Collection - Magnificent Mile
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 £141 per night from 25 May to 26 May
£141
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (3,237 reviews)
"Valet parking was easy and worth the extra money to be able to take your car in and out of it a few times during your stay. Hotel room had great views on the 18th floor with tall ceilings. Room was clean and had everything I needed and lots of space. The bathroom barn door style was sticking at one ..."

Reviewed on 20 May 2026

Aloft Chicago Mag Mile
See all 4,625 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 . 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

875 North Michigan Avenue

875 North Michigan Avenue

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.