Old Town Triangle Holidays from £1,004

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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.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,438, price is now £1,004 per person
£1,004
per person
10 Jul - 14 Jul
found 16 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Great accommodation and staff attention

Reviewed on 8 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,264, price is now £1,493 per person
£1,493
per person
25 Jul - 1 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,403, price is now £1,632 per person
£1,632
per person
25 Jul - 1 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,577, price is now £1,802 per person
£1,802
per person
25 Jul - 1 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great property and location!

Reviewed on 8 May 2026

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 £2,454, price is now £1,735 per person
£1,735
per person
25 Jul - 1 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 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

4 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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £98 per night from 20 May to 21 May
£98
20 May - 21 May
includes taxes & fees
8.2/10 Very Good! (2,696 reviews)
great location

Reviewed on 9 May 2026

Hotel Felix River North/Magnificent Mile
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 £117 per night from 10 May to 11 May
£117
10 May - 11 May
includes taxes & fees
8/10 Very Good! (10,189 reviews)
Room was clean, coffee maker didn’t work but was replaced quickly. Staff all very helpful, especially Steve the doorman/security. Very helpful getting us a cab!

Reviewed on 8 May 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £120 per night from 26 May to 27 May
£120
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,186 reviews)
As soon as we arrived Hotel Staff was very friendly and helpful. Valet parking was very convenient.

Reviewed on 9 May 2026

River Hotel
See all 4,635 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 £1,004, 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

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

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