4-day
Specific Tour
Unlimited
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Chicago, the “Windy City,” is a captivating metropolis perfectly suited for independent exploration. Its efficient public transport and distinct neighborhoods allow you to immerse yourself fully in its dynamic energy and culture at your own pace.
Start at Millennium Park, home to “Cloud Gate” (The Bean) and Crown Fountain. Nearby, the Art Institute of Chicago offers a world-class art collection. For breathtaking views, ascend to Skydeck Chicago at Willis Tower. A Chicago Architecture Foundation Center River Cruise provides unparalleled perspectives on the city’s architectural marvels. Explore the Museum Campus, featuring the Field Museum of Natural History and the Shedd Aquarium. Stroll the Magnificent Mile for upscale boutiques and grand buildings, or visit the free Lincoln Park Zoo for city views and a natural oasis.
Indulge in Chicago’s culinary staples. The legendary deep-dish pizza, with its thick crust and generous layers, is a unique local invention. The famous Chicago-style hot dog is a masterpiece: an all-beef frankfurter “dragged through the garden” with mustard, onions, relish, pickle, tomatoes, sport peppers, and celery salt – crucially, no ketchup! Also, try the Italian beef sandwich, thinly sliced roast beef on an Italian roll, often dipped in its own juices and topped with giardiniera.
Getting around independently is efficient via the Chicago Transit Authority (CTA). The ‘L’ train system connects major attractions and neighborhoods, with many lines operating 24 July. Buses complement the ‘L’, and a Ventra Card simplifies access to both. Walking is excellent for downtown and neighborhood exploration. Ride-sharing services are also readily available for convenience.
The best times for an individual trip are late spring (May-June) and early autumn (September-October). The weather is pleasantly mild, ideal for outdoor activities. Summers (July-August) are vibrant but can be hot and humid. Winters (November-April) are often very cold and snowy, challenging for extensive outdoor sightseeing.
To maximize your time, always book popular attractions, museum tickets, and architectural tours well in advance. This is crucial for Skydeck Chicago, the Art Institute, and river cruises. Pre-booking helps you secure preferred time slots and avoid long queues, giving you more freedom to explore at your leisure.
The trip runs for 4 days and starts from €995 per person. You pick the dates — there is no fixed departure.
The price includes: flight tickets, 1 cabin bag up to 8 kg and 1 personal item, airport taxes, fuel surcharges, 3 nights in a centrally located hotel, VAT.
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From €995 per person
Price per person for 2 people sharing a double room, in low season, with flights from Athens.
This is a starting price. The final price depends on your dates, flights and hotel, and we confirm it in the personal offer we send you. No payment is needed when you send your request.
With this trip you earn about 995 Loyalty points per person (1 point per €1, worth about €10 off a future trip). Points double for bookings completed in January and February. About Lia's Loyalty Club
Add whatever you need around this trip and send us one request. We reply with one final price for the whole trip.
Price and availability last updated: 28 August 2026
No account needed. We will let you know if anything worth knowing happens.
Optional tours, tickets and activities you can book for your days there. We arrange the trip — these you choose yourself.
Activities, experiences and local guides — book ahead and keep your days free of queues.
Compare prices from all major car rental companies, with free cancellation on most offers.
Attraction tickets, airport transfers, rail passes and day trips, booked in advance.
These activities are provided and sold by our partners. You complete the booking on their page, at exactly the same price.
This is a made-to-order trip, so you choose the dates. We are happy to advise on the best season for this destination and on how the weather, prices and crowds change through the year — just tell us roughly when you are thinking of travelling.
The main inclusions are:
The full list of what is and is not included appears in the "Included / Excluded" section on this page.
It depends on the season and the destination. Many trips do have a direct flight, but depending on your dates the airlines may not have a direct connection available for that period, in which case the trip may involve one stopover. We will tell you the exact flight routing clearly in your quote, before you proceed with the booking.
Not necessarily. The "From €X" price is the lowest price available today, based on current flight and hotel availability for that destination. Because availability changes daily, the final price for your specific dates may differ. We'll send you a firm, written quote before anything is charged, once you tell us the dates you have in mind.
Flight and hotel prices change daily depending on season, demand, day of the week, and how far in advance you book. That's why the price shown is indicative — the earlier you tell us your dates, the easier it is for us to secure the best possible price.
The single-room supplement varies by hotel and destination, and is included in the quote you'll receive for your specific dates. If you're travelling alone, let us know from the start so the quote already reflects the correct single-room price.
Payment is due in full at the time of booking. For certain hotels that have their own payment policy (for example a deposit or a specific payment deadline), we'll let you know clearly before you proceed, so you know exactly what applies.
Yes — once your booking is confirmed, the price is fixed and won't be affected by later changes in flight or hotel prices. Availability and price can only change before your booking is finalised.
Several trips offer the option to depart from a city other than Athens (for example Thessaloniki), usually with a small additional charge. If this applies to a specific trip, it will be noted on the page or mentioned when we send your quote.
For this destination you do need a visa, but it's easy to arrange — either online before you travel (e-Visa) or on arrival at the airport, with no embassy visit required. We'll guide you through the process once you book. You'll also need a passport valid for at least 6 months from the return date. Entry rules change from time to time, so please confirm the current requirements with us before you book.
Changes and cancellations follow the terms of the airlines, hotels and suppliers booked for you, so the cost depends on how close to departure you are and on the fare rules of each booking. Tell us as early as possible and we will look for the least costly option. The general terms of participation apply to every booking.
Travel insurance is not included in the price unless the "Included" list on this page says otherwise. We strongly recommend it, especially for trips outside the EU, so that medical care, cancellation and lost luggage are covered. We can arrange a policy for you — just ask when you book.
Yes — this is an individual trip, not a group departure. There is no fixed itinerary and no coach schedule: you travel on your own, at your own pace. We can change the number of nights, the class of hotel, add or drop destinations and arrange transfers, car hire or private guides.
Send us a request through the form on this page, call us, or drop by the office. We will come back with availability and a written quotation before anything is charged. The trip as shown runs for 4 days.
Departure from: Athens · Thessaloniki · Larnaca.
Flights: Usually with one connection.
Visa (Greek citizens): No visa needed; an ESTA electronic authorisation is required before the flight.
Earliest departure: At least 7 days after booking, so the electronic visa or authorisation can be issued in time.
Best time to go: All year round; spring and autumn are the most pleasant.
Travel insurance: We recommend travel insurance with medical and cancellation cover; ask for it together with your quote.
Our office helps you with all of the above, step by step.
Our office helps you with all of the above, step by step.
