Old Town Chicago Holidays from £670

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,030, price is now £670 per person
£670
per person
5 May - 8 May
found 7 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amenities, staff was ok

Reviewed on 25 Feb 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,978, price is now £1,349 per person
£1,349
per person
1 May - 6 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on 26 Jan 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,431, price is now £989 per person
£989
per person
1 May - 6 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on 22 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £916, price is now £675 per person
£675
per person
2 Apr - 7 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on 16 Feb 2026

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was £1,345, price is now £1,016 per person
£1,016
per person
1 May - 6 May
found 17 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (4,159 reviews)
The front desk staff was very helpful and courteous when I checked in. They detailed the many wonderful services available at the hotel.

Reviewed on 25 Feb 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 featuring a city

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 Chicago

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 £78 per night from 27 Feb to 28 Feb
£78
27 Feb - 28 Feb
includes taxes & fees
8/10 Very Good! (9,937 reviews)
Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ...

Reviewed on 26 Feb 2026

Congress Plaza Hotel
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 £129 per night from 1 Mar to 2 Mar
£129
1 Mar - 2 Mar
includes taxes & fees
9.4/10 Exceptional! (3,415 reviews)
To recessed lights in the ceiling near the windows the windows would not shut off. We tried every little light switch in the room eight ways to Sunday and could not get those recessed lights off. The only way to shut them off was to take the card out to stop the electricity in the room. But then ...

Reviewed on 26 Feb 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £89 per night from 4 Mar to 5 Mar
£89
4 Mar - 5 Mar
includes taxes & fees
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on 26 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,729 properties in Old Town Chicago
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
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Family Friendly Holidays

Frequently asked questions

How much does an Old Town Chicago travel package cost?
From as little as £670. 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.

Things to do

Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.