UNITED STATES · ARCHITECTURE & CULTURE

City trip to Chicago

Chicago is America's architecture capital: a stunning skyline along Lake Michigan, deep musical roots (blues, jazz and house), world-famous deep dish pizza and the free Millennium Park with The Bean. KLM and United fly non-stop from Schiphol in around 10 hours.

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Quick answer: KLM and United Airlines fly non-stop from Amsterdam Schiphol (AMS) to Chicago O'Hare (ORD) in approximately 9.5 to 10 hours. Return tickets start around €550 per person. May and September are the best months for weather and price. A 5-to-7-day city trip costs approximately €1,200 to €1,800 per person including flight and hotel.

Updated 19 August 2026

When is the best time to visit Chicago?

May and September are the very best months for Chicago: pleasantly warm (18 to 24 degrees), minimal rain and plenty of events. September is even the driest month of the year. July and August are lively but hot and crowded.

Avoid December through February: Chicago is justly known as the Windy City and winters can be brutal, with wind chill temperatures reaching -20 degrees. Those who want the cheapest flights and quietest museums should choose November or January, but bring a serious winter coat.

Best months
May and September
High season
Jun, Jul, Aug
Temperature (May)
18 to 28 degrees

Top 5 things to do in Chicago

  • Millennium Park and The Bean (free) Cloud Gate, the giant bean-shaped stainless steel sculpture in Millennium Park, is the symbol of Chicago and completely free to visit. The park itself is always open and also features the free Pritzker Music Pavilion, where free outdoor concerts are held in summer. Early morning you can have The Bean almost to yourself.
  • Art Institute of Chicago (around $32) One of the world's greatest art museums, with Seurat's famous A Sunday on La Grande Jatte, Edward Hopper and a large Impressionist collection. Admission around $32 per adult; children under 14 free. Book online for the best price and no queue.
  • Chicago Architecture Center River Cruise (around $50) The most famous way to admire Chicago's iconic skyline. An Architecture Center guide points out 50 buildings and explains styles from Art Deco to Modernism. Book in advance via the website for the best price; the cruise lasts approximately 90 minutes.
  • Lincoln Park Zoo (free) One of the few major urban zoos in the US that is completely free, including gorilla house, polar bear and big cats domain. Combined with the nearby Alfred Caldwell Lily Pool (also free, a National Historic Landmark) it makes for a perfect half-day at zero cost.
  • Willis Tower Skydeck (around $40-60) Views from 412 meters up in the former Sears Tower, featuring the Ledge, a glass-floor box extending 1.2 meters outside the building's perimeter. Impressive on a clear day. Booking online in advance is cheaper than paying at the door.

Flights and transport from the Netherlands to Chicago

Both KLM and United Airlines fly non-stop from Amsterdam Schiphol (AMS) to Chicago O'Hare International Airport (ORD); flight time is approximately 9.5 to 10 hours outbound and approximately 8 hours return. There are approximately 2 daily direct flights combined. Return tickets start around €500 to €650 per person in the low season (November to January). Book at least 2 to 3 months in advance.

There are no intercontinental flights from Eindhoven Airport. Travel to Schiphol (approximately 1.5 hours by intercity train or around 1 hour by car) for the non-stop connection. Alternatives via London, Dublin or Frankfurt extend travel time to 13 to 16 hours and are generally more expensive.

From O'Hare to the city centre: the CTA Blue Line L-train runs 24 hours a day and costs just $2.75 for a 45-minute ride to Clark/Lake in the heart of The Loop. Buy a Ventra Card (similar to an OV-chipkaart) at an O'Hare machine. A day pass costs $6 and a weekly pass $25.

Flight time
Approx. 9.5-10 hrs
Return flight
From approx. €550
Airport
O'Hare (ORD)
L-train to centre
$2.75 (45 min)
Day pass CTA
$6
Weekly pass CTA
$25

How much does a Chicago city trip cost?

Hostels in Chicago cost approximately $30 to $70 per night in a dormitory. Budget hotels start around $100 to $150 per night. Mid-range hotels in The Loop or River North cost $150 to $250. Tip: neighbourhoods like Wicker Park or Logan Square (connected via the Blue Line) offer comparable quality for 20 to 30 per cent less.

Food: an authentic Chicago-style hot dog costs $5 to $8. A portion of deep dish pizza at Lou Malnati's or Giordano's costs $15 to $25 per person. A casual dinner at a good restaurant costs $25 to $40. The CityPASS bundle (around $130) gives access to Willis Tower plus Shedd Aquarium and a choice of other attractions, saving up to 50 per cent versus individual tickets.

Hostel
From $30/night
Mid-range hotel
$150-250/night
Art Institute
Approx. $32
Deep dish pizza
$15-25 p.p.
Week all-in
Approx. €1,200-1,800
CityPASS bundle
Approx. $130

Frequently asked questions about Chicago

When is the best time to visit Chicago?

May and September are the best months: pleasantly warm (18 to 24 degrees Celsius), sunny and less crowded than summer. July and August are warm but busier and more expensive. Avoid January and February: Chicago is known as the Windy City and can be extremely cold (-10 to -15 degrees Celsius, with wind chill even lower).

How do I fly from the Netherlands to Chicago?

KLM and United Airlines fly non-stop from Amsterdam Schiphol (AMS) to Chicago O'Hare International Airport (ORD) in approximately 9.5 to 10 hours. There are no intercontinental flights from Eindhoven; travel to Schiphol (approximately 1.5 hours) for the non-stop connection.

How much does a flight to Chicago from the Netherlands cost?

Return tickets start around 500 to 650 euros per person in the low season (November, January). In high season (summer) expect to pay 1,000 to 1,300 euros. Book at least 2 to 3 months in advance. September is historically the cheapest holiday period.

How do I get cheaply from O'Hare to downtown Chicago?

Take the CTA Blue Line L-train from O'Hare Airport to downtown for just $2.75. The journey takes approximately 45 minutes. This is by far the cheapest and most reliable option compared to a taxi ($45 to $60) or Uber ($35 to $55).

What are the best free things to do in Chicago?

Millennium Park with The Bean (Cloud Gate) is free and an absolute must-see. The Lincoln Park Zoo is one of the few major urban zoos in the US that is completely free. The Riverwalk along the Chicago River is also free. On warm days, the Lakefront Trail along Lake Michigan is beautiful and costs nothing to walk or cycle.

Do I need an ESTA for Chicago?

Yes, Dutch travellers need a valid ESTA to enter the United States. Apply at least 72 hours before departure via the official US government website. An ESTA costs $21 and is valid for 2 years for multiple trips.

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Live availability and prices for hotels in The Loop, River North and Wicker Park.

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