Old Town Chicago Holidays

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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.
  • Pool
    Aug 3 - Aug 8

    Hilton Garden Inn Chicago Downtown South Loop + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.8/10 - Excellent (2,014 reviews)
    "."
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,740
    £2,294
    per traveller
    found 7 hours ago
    Hilton Garden Inn Chicago Downtown South Loop
  • Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels
    Aug 3 - Aug 8

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,398 reviews)
    "Shea was wondering! A couple of hiccups but she handled with ease. I would definitely stay again because of the service I received."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,801
    £2,308
    per traveller
    found 7 hours ago
    Sports Illustrated Resorts Chicago
  • 2 bars/lounges, rooftop bar
    Aug 3 - Aug 8

    theWit Chicago, a Hilton Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Great location. Staff was professional and helpful. Restaurant State and Lake had great breakfast and ambience. Roof at theWit was amazing with a good happy hour, great ambience and vibe with city views."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £4,011
    £2,455
    per traveller
    found 7 hours ago
    theWit Chicago, a Hilton Hotel
  • Meeting facility
    Aug 3 - Aug 8

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,371 reviews)
    "Great stay, very clean and comfortable."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,920
    £2,403
    per traveller
    found 7 hours ago
    Thompson Chicago, by Hyatt
  • Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
    Aug 3 - Aug 8

    Holiday Inn & Suites Chicago - Downtown by IHG + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,006 reviews)
    "Convenient parking and staff were helpful in suggesting restaurants and shopping close by"
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,905
    £2,404
    per traveller
    found 6 hours ago
    Holiday Inn & Suites Chicago - Downtown by IHG

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

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 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 £178 per night from 2 Jun to 3 Jun
£178
2 Jun - 3 Jun
includes taxes & fees
8/10 Very Good! (10,119 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on 27 May 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 £214 per night from 28 Jun to 29 Jun
£214
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (4,275 reviews)
"Terrific location blessed with a wonderful staff. Especially grand breakfast too"

Reviewed on 28 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £135 per night from 28 Jun to 29 Jun
£135
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,484 reviews)
"I had travel delays and a situation with my husband and my luggage and they have been very nice about it . Front desk staff is very kind and professional"

Reviewed on 27 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,637 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% 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
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
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.