Old Town Chicago Holidays from £759
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Old Town Chicago Holiday
If you're wanting a commercial retreat, our Old Town Chicago holiday packages are what you need. Whether you're seeking cafes, bars and pubs or history, this neighbourhood has a bit of something for everyone. Begin your trip to Old Town Chicago by checking out nearby attractions such as Wrigley Field, Millennium Park and Willis Tower. Expedia will help turn your ideal Old Town Chicago holiday into reality, no matter your budget or travel plans.
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
£759
per person
23 Nov - 30 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,884 reviews)
Stayed for 1 night. The staff was very friendly and helpful. Enjoyed the stay. The room was very clean
Reviewed on 11 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
£790
per person
23 Dec - 28 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8/10 Very good! (2,382 reviews)
The staff at the desk were helpful in checking in and holding luggage.
I asked for approval to send a package before I checked in which as approved in writing from the hotel. The package was misplaced and for over a day I spoke to 3 people each time having to explain what I was looking for. The small package was found after I left. I asked that package be sent to a suburb in Chicago. I was told only if I pay for postage. I thought this was unfair. They said they would speak to the management and I never heard. I have never had a quality hotel do this before.
Reviewed on 11 Oct 2026
Where to stay in Old Town Chicago
Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Old Town Chicago
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£104
10 Nov - 11 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£137
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,525 reviews)
"It was convenient and accessible to downtown. The rooms were outdated and felt like it could use some remodels."
Reviewed on 11 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£128
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,475 reviews)
"The staff at the desk were helpful in checking in and holding luggage. I asked for approval to send a package before I checked in which as approved in writing from the hotel. The package was misplaced and for over a day I spoke to 3 people each time having to explain what I was looking for. The small ..."
Reviewed on 11 Oct 2026
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.
Frequently asked questions
How much does an Old Town Chicago travel package cost?
From as little as £759. Yes, you read that right. Our Old Town Chicago travel packages are the best way to make your budget last longer. Bundle your flights, hotels and rental car and get out and see this exciting destination.
If I'm not able to travel, can I cancel my Old Town Chicago travel package?
You can. We get that even the best-laid plans can go awry, so we're happy to help if you need to make changes to your Old Town Chicago travel package. You may be able to change or cancel your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Old Town Chicago?
Bundle, bundle, bundle. Hotels, rental cars and flights — combine whatever you need into an Old Town Chicago travel package and save. Score even bigger bargains when you add extras such as day tours to your booking. But that's not the only impressive part. You have the freedom to put together your holiday your own way. We offer over 550 partner airlines and 1,000,000 properties across the globe, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Old Town Chicago holidays?
Expedia has partnered with online lender Klarna to make booking your next break easier on your bank balance. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more money to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Browse these flexible payment options:
- Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can have 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 from Klarna.
- Low deposit holidays: When you stumble on an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you secure your getaway.
Where should I stay in Old Town Chicago?
Most visitors who travel to Old Town Chicago include Millennium Park and Wrigley Field on their bucket lists. Why not select a hotel right near these popular attractions?
What are the top hotels in Old Town Chicago?
Get your trip off to a great start by booking a room at Hyatt Regency Chicago. It's one of most sought-after hotels in Old Town Chicago. Another option is The Godfrey Hotel Chicago.
How far in advance should I book my Old Town Chicago holiday?
It can be difficult to know when is the ideal time to book your Old Town Chicago holiday. But typically the earlier you book, the better the prices. In some cases, you can book your flights and hotels up to a year before departure. If you're eager to escape on a last-minute getaway, no need to stress! There are great deals announced on Expedia every day.
What does an Expedia Old Town Chicago travel package include?
That depends on what sort of trip you want to have. Old Town Chicago travel deals can include car rentals, flights and hotels. You can mix and match to find the bundle that suits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Old Town Chicago travel package?
Booking all the parts of your holiday together is one of the best ways to save. Bundle your car rentals, flights and hotels into one little package. But your options don't end at hotels. Expedia has all kinds of properties, including holiday rentals like oceanfront condos and city residences. Your choices are almost endless!
Can I choose my airline with an Old Town Chicago Expedia travel package?
Yes — that's the beauty of an Expedia package. You're in charge! We have more than 550 airline partners across the globe, so you have lots of choice when planning your Old Town Chicago getaway.
Stay near popular Old Town Chicago attractions
Second City
9.6/10 (15 reviews)
You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Lighthouse ArtSpace Chicago
You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your travels in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.
Henry Gerber House
Learn about the local history of Chicago when you take a trip to Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.
Midwest Buddhist Temple
After visiting Midwest Buddhist Temple, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the shops in this vibrant area.
House of Glunz
8.4/10 (6 reviews)
You can find the perfect gifts to bring home at House of Glunz during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Hudson Chess Park
Explore the great outdoors at Hudson Chess Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
* 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.