Old Town Triangle Holidays from £1,165

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Your Old Town Triangle Holiday

Whatever your travel style, you can see and do more with a customized Old Town Triangle holiday package. Spend your getaway enjoying this neighbourhood's history and its other delights. Kick off your trip to Old Town Triangle by heading to nearby attractions such as Wrigley Field, Millennium Park and Willis Tower. Whatever your travel goals or the size of your budget, booking the ultimate Old Town Triangle holiday is simple with Expedia.

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,545, price is now £1,165 per person
£1,165
per person
3 Sept - 7 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!

Reviewed on 18 Jun 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was £1,809, price is now £1,412 per person
£1,412
per person
27 Aug - 3 Sept
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it.

Reviewed on 31 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,469, price is now £1,948 per person
£1,948
per person
30 Jul - 3 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great customer service! Let us in in the morning even our check in time was afternoon. Views were incredible!

Reviewed on 23 Jun 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,888, price is now £1,547 per person
£1,547
per person
30 Jul - 3 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on 21 Jun 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,700, price is now £1,403 per person
£1,403
per person
15 Aug - 20 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on 19 Jun 2026

Where to stay in Old Town Triangle

Find the best Old Town Triangle areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Triangle
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 Old Town Triangle

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £122 per night from 29 Jun to 30 Jun
£122
29 Jun - 30 Jun
includes taxes & fees
8/10 Very good! (10,167 reviews)
"Room smelled a little like mold or sitting water although the floors were never and the room was clear overall. The shower had a lot of rust in it. Hotel does not offer parking and the garage they recommend is was already full."

Reviewed on 23 Jun 2026

Congress Plaza Hotel
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 £125 per night from 7 Jul to 8 Jul
£125
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,465 reviews)
"Great location, rooms and service"

Reviewed on 23 Jun 2026

Hilton Chicago/Magnificent Mile Suites
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 £113 per night from 30 Jun to 1 Jul
£113
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,615 reviews)
"Stunning room, lobby, and spectacular views from the rooftop lounge. That being said, room service could’ve been more attentive. We asked for body wash for our room, as it was out when we checked in. Even after calling the front desk, this small request went unanswered. Barring that, it was a good ..."

Reviewed on 23 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,643 properties in Old Town Triangle
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.
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Frequently asked questions

How much does an Old Town Triangle travel package cost?
Starting from as little as £1,165, you can create your own Old Town Triangle package the way you want. Simply bundle hotels, flights and rental cars and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Old Town Triangle travel package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Old Town Triangle?
Our Old Town Triangle travel packages offer plenty of savings for the savvy globetrotter. For the best deals, simply combine your hotel, flights and extras (such as activities) into a budget-friendly package. But cheap prices are just the beginning of your next epic adventure. When you book with Expedia, you'll have more than 550 airlines and 1,000,000 properties across the globe to pick from. Whatever your budget, there's a travel package with your name on it.
Does Expedia offer Book Now, Pay Later Old Town Triangle holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday over multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Simply put down a small deposit on your escape and then start working on your travel itinerary.

Where should I stay in Old Town Triangle?
A visit to Old Town Triangle isn't complete without stopping by Millennium Park and Wrigley Field. Stay nearby so you can easily access these popular attractions.
What are the top hotels in Old Town Triangle?
Secure a room at Hyatt Regency Chicago. It's one of the area's most sought-after properties. Another top option in Old Town Triangle is The Godfrey Hotel Chicago.
How far in advance should I book my Old Town Triangle holiday?
To land rock-bottom prices, book as soon as you can. Air carriers generally advertise flights, along with some of the lowest fares, up to a year ahead of time. Hotels, car rental and activities should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway in Old Town Triangle, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Old Town Triangle travel package include?
That depends on what sort of escape you have in the works. Old Town Triangle holiday deals can include hotels, car rentals and flights. You can mix and match to find the package that suits you. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Old Town Triangle travel package?
You'll score impressive savings when you bundle your flights, hotels and rental cars into a package. Not just that, booking everything in one place makes trip planning easier. So why waste money or time? Whether you're putting together a luxury city stay with your love or a budget solo adventure, have a look at our travel packages today.
Can I choose my airline with an Old Town Triangle Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our travel packages give you the freedom to pick from available flights, hotels and activities that suit you.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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 C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.