Old Town Triangle Holidays from £917

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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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Excellent establishment great staff very clean and spacious

Reviewed on 5 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 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
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (270 reviews)
walkable to many desireable places.

Reviewed on 16 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 24 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
The Breakfast Buffet ( included with your stay ) was a real surprise. Reminded us of the ones when we stay at all inclusive resorts when it comes to breafast options. The food was fantastic and the staff was very attentive cleaning and seating everyone quickly. Rooms were really nice, comfortable bed, bathroom was laid out really well. Super clean hotel that we would definitely recommend & stay at again when returning to Chicago

Reviewed on 7 Aug 2025

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 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 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 £118 per night from 1 Sept to 2 Sept
£118
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,974 reviews)
"Great location! Rooms are newly renovated and nice."

Reviewed on 5 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £171 per night from 22 Aug to 23 Aug
£171
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
"Great!"

Reviewed on 5 Aug 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is £129 per night from 24 Aug to 25 Aug
£129
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,345 reviews)
"My wife and daughter loved there was a Starbucks a short walk down the street, maybe 5 minutes, this was their morning routine. The restaurant was good, prices were in line with other spots in the area, however, I did not like being told the restaurant closes at 9:30, even though hours say 10. Not ..."

Reviewed on 5 Aug 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,673 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Old Town Triangle travel package cost?
Starting from as little as £917, 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

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

£22
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

£33
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.