Chicago
Chicago is the ultimate American city, welcoming visitors to a one-of-a-kind experience. Stroll the downtown streets of one of the most walkable cities in the U.S. and explore block after block of outstanding architecture that makes up Chicago’s breathtaking skyline.
At a glance
- On the shores of Lake Michigan
- Stunning architecture
- Award winning restaurants, theatre and music
-
-6 hours
Time Difference -
English
Language Speaking -
9 hours
Flight Time -
$USD
Currency -
Chicago O'Hare International (ORD)
Nearest Airport
Special Offers
Take a look at our current special offers

Low Deposit Offer
Book by 30th September and secure your booking with a deposit of just £150pp
Low deposit offer of £150pp on holidays departing between 2nd September 2025 and 31st October 2027. Book by 30th September 2025.
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10GB of FREE data
Stay connected with up to 10GB of FREE data
Stream, surf, and share more with up to 10GB data on us. Book by 30th September 2025.
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Included Rail Upgrade
Enjoy an included service upgrade on two day rail holidays.
Book a two day rail holiday in the American West and get an included service upgrade. Rail tours sell out quickly so book now to avoid disappointment. Book by 30th September 2025.
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Save up to £500 per booking
Book by 30th September and take advantage of our exclusive savings
Book your next American adventure by 30 September 2025 and you can save up to £500 per booking. You’ll save:
• £500 on bookings over £10,000
• £350 on bookings between £7,500-£9,999
• £300 on bookings between £5,000-£7,499
• £250 on bookings between £2,500-£4,999
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Discounted Hotel Rates
Receive up to a 40% discount on hotel stays
Save up to 40% across our extensive hotel range. Offer valid for selected dates and hotels for the 2025/2026 seasons. Book by 15th October 2025.
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Best time to visit Chicago
The best time to visit Chicago is during the spring (April to June) and autumn (September to early November). These seasons offer mild and pleasant weather, fewer tourists, and a variety of events and activities to enjoy.
Spring (April to June) is a fantastic time to explore the city. The weather is mild, with temperatures ranging from 7°C to 24°C, making it perfect for outdoor activities. During this period, you can enjoy events like the Chicago Flower & Garden Show and the St. Patrick's Day Parade. The city's parks and gardens come to life with blooming flowers, providing a beautiful backdrop for sightseeing and leisurely strolls.
Autumn (September to early November) is another excellent time to visit Chicago. The temperatures are comfortable, ranging between 10°C and 21°C, making it ideal for exploring the city on foot. Fall also brings a variety of events, such as the Chicago International Film Festival, Oktoberfest, and Halloween celebrations. The city's parks and streets are adorned with stunning fall foliage, perfect for scenic walks and photography.
Both spring and autumn provide an excellent balance of enjoyable weather and engaging activities without the extreme temperatures of summer and winter, making them the best times to visit Chicago.
Average temperatures by month
- JAN -6°
- FEB -4°
- MAR 3°
- APR 10°
- MAY 15°
- JUN 21°
- JUL 23°
- AUG 22°
- SEP 18°
- OCT 12°
- NOV 5°
- DEC -3°
Contact our travel experts to start planning your holiday to Chicago
Contact usRecommended Chicago holidays
Explore a collection of our handpicked holidays to Chicago below

Architecture, Music & The French Quarter
This holiday showcases the USA’s rich musical heritage of bluegrass, country, rock 'n' roll, rhythm 'n' blues and soul.
10 Nights From
£1,272
ppOverview
This holiday showcases the USA’s rich musical heritage of bluegrass, country, rock 'n' roll, rhythm 'n' blues and soul.
What’s included?
- International flights from the UK in economy class
- Accommodation for 9 nights
- Amtrak from Chicago to Memphis and Memphis to New Orleans in Coach class

Route 66 – Classic Americana
Passing through eight states and covering three time zones, Route 66 is the classic self-drive trip that gives great insight into a journey well-travelled.
15 Nights From
£1,893
ppOverview
Passing through eight states and covering three time zones, Route 66 is the classic self-drive trip that gives great insight into a journey well-travelled.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 15 nights
- 14 days intermediate car hire with fully inclusive insurance, unlimited mileage and taxes

Great Lakes Explorer
Centred around some of the world’s most amazing natural wonders, this trip will take you to three of the Great Lakes and Great Lake states
13 Nights From
£1,948
ppOverview
Centred around some of the world’s most amazing natural wonders, this trip will take you to three of the Great Lakes and Great Lake states
What’s included?
- International flights from the UK based on economy class
- Accommodation for 13 nights
- 12 days intermediate car hire with insurance coverage, unlimited mileage and taxes

America's Music Cities
Travel from the windy city of Chicago, along famous Route 66 to New Orleans the home of jazz music. Other highlights include the music cities of Memphis, Nashville, and Muscle Shoals.
15 Nights From
£2,196
ppOverview
Travel from the windy city of Chicago, along famous Route 66 to New Orleans the home of jazz music. Other highlights include the music cities of Memphis, Nashville, and Muscle Shoals.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 15 nights
- Graceland Elvis Experience Tour including Airplanes
- 10 days intermediate car hire with insurance coverage, unlimited mileage, and taxes

The Ultimate Michigan & Great Lakes Explorer
This trip will take you to all five of the Great Lakes including three Great Lake States plus the Canadian Province of Ontario. From pristine waters to remarkable national parks, there is so much to explore and discover on this amazing holiday.
16 Nights From
£2,448
ppOverview
This trip will take you to all five of the Great Lakes including three Great Lake States plus the Canadian Province of Ontario. From pristine waters to remarkable national parks, there is so much to explore and discover on this amazing holiday.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 16 nights
- 15 days compact car hire with fully inclusive insurance, unlimited mileage and taxes

Discover Route 66 by Rail
Ride the rails from Chicago to Los Angeles and get your kicks on Route 66.
15 Nights From
£2,656
ppOverview
Ride the rails from Chicago to Los Angeles and get your kicks on Route 66.
What’s included?
- International flights departing from the UK based in economy class
- Accommodation for 15 nights
- Amtrak train from Chicago to St Louis in Coach class
- Amtrak overnight train from St Louis to Albuquerque in Coach class
- Amtrak train from Albuquerque to Flagstaff in Coach class
- Return Amtrak transfers from Flagstaff to Williams
- Amtrak overnight train from Williams to Los Angeles in Coach class
- One day Chicago Hop on/off Bus tour
- 90-minute St Louis Narrated Trolley Tour
- Round trip Grand Canyon Railway from Williams to the Grand Canyon
- One day Los Angeles Hop-on Hop-off Bus tour

Journey Across the USA by Rail
Perfect for rail enthusiasts and for non-drivers this epic coast to coast rail tour includes the iconic and much-loved cities of New York, Washington DC, Chicago, Los Angeles and San Francisco and the awe-inspiring wonder of the Grand Canyon.
18 Nights From
£3,426
ppOverview
Perfect for rail enthusiasts and for non-drivers this epic coast to coast rail tour includes the iconic and much-loved cities of New York, Washington DC, Chicago, Los Angeles and San Francisco and the awe-inspiring wonder of the Grand Canyon.
What’s included?
- International flights departing from the UK in economy class.
- Accommodation for 18 nights
- Amtrak train from New York to Washington DC in Coach Class
- Amtrak overnight Floridian from Washington DC to Chicago staying in a roomette
- Amtrak overnight Southwest Chief from Chicago to Flagstaff staying in a roomette
- Amtrak overnight Southwest Chief from Flagstaff to Los Angeles staying in a roomette
- Amtrak Coast Starlight from Los Angeles to Emeryville in Coach Class
- Amtrak coach from Emeryville to San Francisco
- One day hop on/off bus tour of New York
- One day hop on/off bus tour of Washington DC
- One day hop on/off bus tour of Chicago
- Full day Grand Canyon tour from Flagstaff
- One day hop on/off bus tour of Los Angeles
- Two day hop on/off bus tour of San Francisco including Alcatraz

Chicago, Beale Street, The Mighty Mississippi & New Orleans
A journey taking you from cosmopolitan Chicago through to the southern states of the US by rail and on river, visiting places that shaped world music and left no-one untouched!
17 Nights From
£6,148
ppOverview
A journey taking you from cosmopolitan Chicago through to the southern states of the US by rail and on river, visiting places that shaped world music and left no-one untouched!
What’s included?
- International flights from the UK in economy class
- Accommodation for 8 nights
- Amtrak from Chicago to Memphis in a bedroom accommodation
- 1 night pre-cruise hotel accommodation including breakfast in Memphis
- 7 nights on board American Cruise Lines in an outside cabin
- All inclusive on American Cruise Lines including all meals, snacks, non-alcoholic and selected alcoholic beverages
- Shared transfer between Memphis hotel and cruise terminal
- One standard shore excursion in each port of call
- Gratuities on board American Cruise Lines
Explore Chicago
Discover Chicago's top attractions with our interactive map
City / Destination
Point of interest
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Snapshot of Chicago
Discover the magic of Chicago, where striking architecture meets a rich cultural scene and exceptional cuisine. From its iconic skyline and lakeside strolls to immersive museums and legendary deep-dish pizza, Chicago offers a unique adventure for every traveller.
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