Hassle-Free Booking
Our user-friendly platform allows you to quickly compare prices, select preferred options
Exclusive Offline Deals
We'll Beat Any Quote!
Found a package elsewhere? We'll beat it.
We have exclusive hidden offers not listed online.
Get in touch to unlock our lowest rates.
Fill Out the Form or Reach Us Directly
Send Us Your Inquiry
UK's Top Rated Travel Agency
Cheap Holidays to Chicago
Cheap Holiday Makers provides cheap holiday packages to Chicago from the UK in 2026/2027. Look through 3-star, 4-star, and 5-star hotel packages to visit Chicago's best neighborhoods like the Loop, Wicker Park, and Lincoln Park. Be sure to stop by Millennium Park, Willis Tower, and Navy Pier. Sample some pizza, take a cruise, and check out the nightlife with the Jazz and Blues tour. The best way to experience the city is on the lakefront tour, taking you through Lake Michigan and Michigan Avenue. Direct flights leave from London, Manchester, and Birmingham and take about 9 hours. UK travelers need an ESTA, not a visa. ATOL-protected (Licence 11375), with fast assistance guaranteed.
3-Star Chicago Holiday Packages
Chicago Baymont by Wyndham Glenview Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Baymont by Wyndham Glenview
Tours (On Request)
Tour Included Chicago River, Hop-On Hop-Off Sightseeing Tour, Sky deck...
From £820/pp
Call Us
Now
Travelodge By Wyndham South Holland Chicago Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Travelodge By Wyndham South Holland
Tours (On Request)
Tour Included Chicago Crime and Mob Bus Tour, Chicago Walking Tour, Chicago F...
From £810/pp
Call Us
Now
Travelodge By Wyndham South Holland Chicago Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Travelodge By Wyndham South Holland
Tours (On Request)
Tour Included Walking tour of Chicago’s gangsters, Chicago River Archit...
From £835/pp
Call Us
Now
4-Star Chicago Holiday Packages
Doubletree by Hilton Lisle Naperville Chicago Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Doubletree by Hilton Lisle Naperville
Tours (On Request)
Tour Included Walking tour of Chicago’s gangsters, Chicago River Archit...
From £930/pp
Call Us
Now
Ambassador Chicago JDV by Hyatt Chicago Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Ambassador Chicago Part Of Jdv By Hyatt
Tours (On Request)
Tour Included Chicago River, Big Bus Chicago, Sky deck Chicago, Field Museum...
From £900/pp
Call Us
Now
Doubletree by Hilton Lisle Naperville Chicago Holiday Tour
Flight
Transport
Hotel
7 Nights
|
8 Days
Doubletree by Hilton Lisle Naperville
Tours (On Request)
Tour Included Chicago Crime and Mob Bus Tour, LEGOLAND Discovery Centre, And...
From £890/pp
Call Us
Now
5-Star Chicago Holiday Packages
Best & Quick Way To Book Is To Call Us
We also have special fares that we are unable to promote online. Call and ask our flight agent to provide you more cheaper option.
Mon - Fri : 9:00AM - 6:00PM | Sat : 10:00AM - 4:00PM
- — Lowest price guarantee.
-
—
All prices are subject to availability.
(Extremely Limited) - — Excellent customer services.
- — All calls answered on top priority
- — All call answered immediately.
SPECIAL OFFER
BOOK NOW PAY LATER
Now you can book your flight with
BASIC DEPOSIT OF £50
Start Your 2026 Travel Journey with a Trusted, ATOL-Protected Travel Agency
Cheap Holiday Makers is a leading UK-based Travel Agency, fully ATOL protected with ATOL Licence (11375). As an ATOL-verified agency, we strictly adhere to all regulatory requirements, giving our clients complete peace of mind when booking with us. Thousands of customers have placed their trust in us and we are proud to deliver reliable, transparent and professional service at every stage of the journey.
ATOL protection safeguards your financial security and ensures your booking is protected under UK travel regulations. You can easily verify Cheap Holiday Makers' ATOL status by:
- Visiting the official CAA ATOL website and entering our ATOL number 11375
- Requesting your ATOL Certificate after booking, which is automatically issued with every ATOL-protected holiday
Our experienced team manages every aspect of your Holiday journey from visa processing and flight reservations to hotel accommodation and ground transportation. Planning Holiday from the UK can feel overwhelming, but we ensure a smooth, well-organised, and spiritually focused experience from start to finish.
At cheapholidaymakers.co.uk, we provide cost-effective Holiday packages from UK, tailored to suit a wide range of budgets and travel needs, without compromising on service quality.
Frequently Asked Questions
Q1. When's the best time to visit Chicago?
Late spring (May–June) and early autumn (September–early October) tend to offer the most pleasant weather, with warm days, manageable crowds, and Chicago's outdoor architecture cruises and riverwalk at their best. Summer (July–August) is peak season, hot and lively with festivals like the Taste of Chicago, but also the priciest and busiest time to book. Winter is a different experience entirely genuinely cold, often well below freezing- but it's also when flights and hotels are cheapest, and the city leans into it with ice skating at Millennium Park and festive light displays.
Q2. How many days do you need in Chicago?
Most of our Chicago packages run 7 nights/8 days, which gives you plenty of time to cover the Loop, Millennium Park, Navy Pier, a Willis Tower Skydeck visit, and at least one or two museums without rushing. If you're short on time, 3–4 days can still cover the highlights, but the longer stay suits those wanting to properly explore neighbourhoods beyond downtown too.
Q3. How much does a holiday to Chicago cost from the UK?
Our Chicago packages start from £810pp for a 3-star stay at Travelodge by Wyndham South Holland, with 4-star options like Ambassador Chicago (part of JdV by Hyatt) from £900pp, both including flights, transfers and hotel stays across a 7-night trip. We also hold exclusive offline deals not listed on the site, so it's always worth calling to see if we can beat a quote you've found elsewhere.
Q4. What's included in a Chicago holiday package?
Our packages include return flights, hotel accommodation and transfers, with 22kg checked baggage and 10kg hand luggage as standard. Optional tours are available on request too, from the Chicago Architecture River Cruise and Willis Tower Skydeck, to Navy Pier, Millennium Park & Cloud Gate (the famous "Bean"), the Field Museum, Shedd Aquarium, and even a Chicago Crime and Mob Bus Tour for something a bit different.
Q5. What's the best way to get around Chicago?
The "L" train (Chicago's elevated rail system) is the easiest way to reach most major attractions, running through downtown and out to the neighbourhoods, and it's generally safe and straightforward to use. Central sights like Millennium Park, the Riverwalk and the Magnificent Mile are also easily walkable from most downtown hotels, so you won't need a car for a city-based trip.
Q6. What food should I try in Chicago?
Deep-dish pizza is the essential Chicago food experience: thick, cheesy, and worth the wait at one of the city's famous pizzerias. Beyond that, the Chicago-style hot dog (never with ketchup, if you ask a local) and Italian beef sandwiches are must-tries, and the city's food scene reflects its diversity well beyond the classics.
Q7. Do UK citizens need a visa for Chicago?
No full visa is required for most trips. UK passport holders can travel under the ESTA (Electronic System for Travel Authorisation) for stays of up to 90 days, covering tourism to Chicago the same as anywhere else in the US. Apply online at least 72 hours before you fly. We also offer a fast visa service if you'd rather have the paperwork sorted for you.
Choose Cheap Holiday Makers
For your next adventure and let the journey begin!
Low Price Packages
Our packages are budget-friendly as we emphasise your comfort, cost and peace of mind over everything. Our main job is to empower our clients according to their requirements.
Trusted Travel Agency
Your safety and satisfaction are paramount. To this end, we offer secure payment options and are fully licensed and protected by ATOL
We are best
Why Choose Us
Flexible Payment Plan
We offer flexible payment options which gives you control over how and when you pay to make booking your travel easy and affordable.
Reliable Customer Support
Our dedicated team is here to provide prompt and reliable assistance 24/7 to ensure that your travel experience is smooth and hassle-free.
Pay Securely
Your financial security is essential. Book your trip with confidence knowing that our secure payment methods protect your personal and financial information.
About us
We specialize in creating budget-friendly holiday packages
From booking your flights and accommodations, We offer budget-friendly holiday packages that promise excitement, relaxation, and exploration so you can focus on making memories that will last a lifetime.
International Tours
Looking to explore new destinations with your squad? Our customizable tour packages are perfect for groups of friends seeking adventure and excitement.
Multiple Options to Choose
We're passionate about helping you explore the world and create unforgettable experiences. Our commitment to excellence ensures a memorable and safe travel experience.
You may also like
-
Baan Khun Nine Holiday Package
Flight Transport Hotel6 Nights | 7 DaysBaan Khun Nine
Tours (On Request)Tour included Pataya Coral islanad, Family Park Pattaya, Pattaya Floating Mar...
From £879/ppCall Us Now -
Bella Villa Cabana Holiday Package
Flight Transport Hotel6 Nights | 7 DaysBella Villa Cabana
Tours (On Request)Tour included Pataya Coral islanad, Nong Nooch Tropical Garden, Family ...
From £885/ppCall Us Now -
Mandhoo Retreat Maldives Holiday Package
Flight Transport Hotel6 Nights | 7 DaysMandhoo Retreat Maldives
Tours (On Request)Tour included Mandhoo Islanad Beach, Local Island Life, Coral Reef Snorkellin...
From £941/ppCall Us Now -
Avyanna Gulhi Beach Maldives Holiday Package
Flight Transport Hotel6 Nights | 7 DaysAvyanna Gulhi Beach Maldives
Tours (On Request)Tour included Gulhi Beach, Bikini Beach, Snorkelling and Diving Spots and man...
From £944/ppCall Us Now -
Karanga Bungalows Holidays Package
Flight Transport Hotel11 Nights | 10 DaysKaranga Bungalows
Tours (On Request)Tour included Stone Town, Paintball and Gell Balster, Zanzibar Spice Tour, Se...
From £980/ppCall Us Now -
Shamba Village Holiday Package
Flight Transport Hotel8 Nights | 7 DaysShamba Village
Tours (On Request)Tour included Stone Town, Private Walking Tour, Paintball and Gell Balster, Z...
From £1,025/ppCall Us Now -
Stay Mikado Maldives Holiday Package
Flight Transport Hotel6 Nights | 7 DaysStay Mikado Maldives
Tours (On Request)Tour included Thimarafushi Beach, Snorkelling and Diving Spots Surf Spots and...
From £1,136/ppCall Us Now -
Zanzibar House Holiday Package
Flight Transport Hotel10 Nights | 11 DaysZanzibar House
Tours (On Request)Tour included Stone Town Private walking tour, Painball and Gell Blaster, Zan...
From £1,200/ppCall Us Now
What Customer Say About Us
-
HamsThanks to Adeem he helped me in booking my holiday to Turkey that suited my budget and included the transportation so I don’t worry about it. The communication was clear and up to standard.
-
Rashhh Rhxiaa
Excellent holiday we had in turkeyi antalya thanks to Eman who orgainsed everything from transfers both way and the hotel.
-
SANA HAMEED
We received services from holiday makers who were completely satisfied, and Syed Shan Ali Zaidi was a really helpful and responsive person. We are grateful for that. Recommended 100 percent.
-
M Aslam
Thanks to Adeem for booking us a family holiday to Turkey Alanyah, beautiful place alhumdulilah.
-
Harmeet Singh Khaneja
Booked always holidays with them Eman helped me alot and always there for us To help and make it easy to fly with easy mind Looking forward to book more from them and thank you eman for great service
Things To Do in Chicago
Explore Best Experiences in Chicago
Adler Planetarium Tour
Chicago Riverwalk Tour
Wrigley Field Stadium Tour
Lincoln Park Zoo Tour
Field Museum Tour
Shedd Aquarium Tour
Museum of Science and Industry
Lake Michigan Sightseeing Cruise
Navy Pier Experience
Millennium Park & Cloud Gate Tour
Chicago Architecture River Cruise
Willis Tower Skydeck Experience
Top Popular Hotels in Chicago
Travelodge By Wyndham South Holland
Travelodge By Wyndham South Holland
Baymont by Wyndham Glenview
Doubletree by Hilton Lisle Naperville
Ambassador Chicago Part Of Jdv By Hyatt
Doubletree by Hilton Lisle Naperville
Flights from the UK to Chicago for 2026/2027
You can fly directly into O’Hare from London, but you would need to connect from other airports in the UK.
|
Departure City |
UK Airport |
Flight Type |
Arrival Airport |
Approx. Flight Time |
Airlines |
|
London |
Heathrow (LHR) |
Non-Stop |
O'Hare (ORD) |
~8h 40m–9h |
American Airlines, British Airways, United Airlines |
|
Manchester |
Manchester (MAN) |
1-Stop |
O'Hare (ORD) |
~11–14h total, via a stopover hub |
Virgin Atlantic (via London), United, American |
|
Birmingham |
Birmingham (BHX) |
1-Stop |
O'Hare (ORD) |
Varies by connection |
Connecting via London or a European hub |
