Chicago
United States
The city that invented the skyscraper, on a lake with a horizon
Photo by Jeff Brown on Unsplash
Photos by Alex Azabache, Tim Gouw, Benjamin R. and Benjamin R. on Unsplash
Best time to visit all of United States
May to October (January is -6°C with wind off the lake)
Climate month by month
The next sixteen daysOpen-Meteo
Average high and low · °C
Rainfall · mm per month
Best months to visit This month · wettest 100mm in May
Where it is
41.88°N, 87.63°W Open in Google Maps
Things to do
A week easily- Take the architecture boat tour, which is the single best thing here
- Spend half a day in the Art Institute
- Walk or cycle the Lakefront Trail
- See a game at Wrigley, which is a hundred and ten years old
- Eat an Italian beef standing up at Al's or Johnnie's
Chicago travel tipsthe general rules
Currency budget United States
ExpensiveDollars and cards for everything. Illinois adds 10.25% sales tax in the city and it is not on the shelf price, and restaurant tipping of 18–22% is not optional in practice.
ATMs & cards
Chase, Bank of America and Fifth Third machines are everywhere. The standalone machines in bars and corner shops charge three to five dollars.
Avoid these
- the standalone machines in bars and corner shops, at three to five dollars a time
Use these instead
- Chase
- Bank of America
- Fifth Third
Cards work everywhere. The 10.25% sales tax is added at the till and restaurant tipping of 18–22% is expected rather than optional.
Wherever you are: if the machine offers to charge you in your home currency, decline. That is dynamic currency conversion and the rate is set by the ATM's operator, not your bank.
Safety all of United States
Reasonably safeThe tourist areas — the Loop, River North, Lincoln Park, Wicker Park, Hyde Park — are safe and busy. Chicago's violence is real and is concentrated in specific South and West Side neighbourhoods that no visitor has reason to be in. The practical risks downtown are phone snatching and car break-ins.
Where to walk, and where to pay attention (8 areas)
Comfortable, including after dark
Worth more attention
- Phone snatching downtown and on the Red Line late at night
- Car break-ins, particularly near the lakefront trailheads
- The wind and the cold in January, which is -6°C before the wind chill and is a genuine hazard
Chicago’s violence is real and is concentrated in specific South and West Side neighbourhoods that no visitor has reason to be in. The tourist core is busy and policed.
Our own assessment, not a sourced index.
Entry & visa United States visa rules
Travel authorisation requiredup to 90 days$40
ESTA under the Visa Waiver Program. Romania was admitted in 2025 and then suspended again, so Romanian passports currently need a full visa — this one has flipped twice, so check the official link rather than trusting anything written down, including this. Bulgaria and Cyprus have never been in the programme. ESTA is refused if you have travelled to Cuba, Iran, Iraq, North Korea, Sudan, Syria, Libya, Somalia or Yemen since 2011 — those trips mean a full visa instead.
Other passports
No visa neededup to 180 days
Visa required in advance$185
A B1/B2 visitor visa, with an in-person interview. Waiting times run to many months in some countries — start early.
How to get it: Apply for ESTA at esta.cbp.dhs.gov at least 72 hours before travel. Every other site charging for this is a reseller.
Entry rules change often and depend on your passport, not where you live — the official page above is the authority, and the airline checks before you board.
Before you fly: travel authorisation
ESTARequired
At least 72 hours before you fly. Most come back in minutes, some take days.
Have these in front of you before you start:
- passport
- a credit or debit card
- your employer's name and address
- any other citizenships you hold
The page calls itself the "Official ESTA Application Website" in its own title, because the trade in charging for this is large. Valid two years, not per trip.
Use the official link above. Sites that charge a "service fee" to submit one of these for you are not the government, and they want the same passport details the real form does.
Health & emergencies all of United States
LimitedRequired to enter
No vaccinations are required for entry from Europe or North America.
Jabs worth having, and what happens if you need a doctor
Worth having
- Routine vaccinations up to date
Getting treated
The care is excellent and the bill is the risk. There is no universal system, an ambulance ride alone can run into four figures, and an uninsured hospital stay can be genuinely ruinous. Comprehensive travel insurance with a high medical limit is essential — this is the one destination where skipping it can cost more than the trip by an order of magnitude.
Orientation, not medical advice — entry rules change and what you need depends on your own history. Check with a travel clinic four to six weeks before you go.
Food tip
Very goodDeep dish is a tourist food and Chicagoans will tell you so; the local pizza is thin and cut in squares. What to eat instead: an Italian beef, dipped, with giardiniera. A Chicago dog, and never with ketchup. And the city has one of the best restaurant scenes in America once you leave the Loop.
Nightlife
Blues and jazz clubs with real lineage, dive bars that have not changed since the fifties, and a river of rooftops in summer.
- Wicker Park — and Logan Square, for the bars
- River North — the mainstream night, and the rooftops
- Green Mill — the jazz club Capone drank in, still going
- Buddy Guy’s Legends — the blues, from the man himself
Closing: 02:00, and 04:00 or 05:00 for the late-licence bars.
A beer in a bar: $7–10
Getting around
Easy- UberWorks here
- LyftWorks here
- BoltNot here
- From the airport
- JFK to Manhattan $70–95 by app, against a flat $70 yellow-cab fare plus tolls
- Against a taxi
- In most American cities there is effectively no taxi trade left to compare with.
The price on the screen is before tip, and a tip is expected.
Time zone and your working day
America/Chicago — 1 hour behind you
7 hours of overlap with a 09:00–17:00 day where you are — 10:00–17:00 your time, 09:00–16:00 theirs.
No overlap with a 09:00–17:00 day where you are. Working from here means one of you keeps odd hours — their day starts at 10:00 on your clock.
office hours both at once night
Their 09:00–17:00 is 10:00–18:00 on yours.
The difference from the UK, Europe, the US and ten more
Worked out against America/New York, which is where this request looks like it came from.
Internet speedall of United States
Why these are United States's numbers and not Chicago's
Home broadband — Fast. Several people on calls at once, large uploads, 4K. Broadband here runs at 2.4× the global median of 130 Mbps.
Mobile data — Fast. Enough to work from a cafe or a beach on a hotspot all day. Mobile runs at 1.7× the global median of 109 Mbps.
Ookla publishes no separate figure for Chicago, so these are medians for all of United States. Cities usually beat the national number and remote islands and national parks fall well below it — treat this as the country's shape, not as a measurement of the street you will be staying on.
A median is the middle of every connection tested there, old copper and new fibre together — so in a country part-way through laying fibre it sits well below what a fibre line actually delivers, and a rental on one can run several times this number. Half of the connections are slower; a fibre flat is rarely one of them. It says what a place can do, not what your rental does, so every listing on Holistay carries its own measured speed and the date it was tested.
Getting online: Airalo or Holafly — a data eSIM for United States, installed before you fly and working the moment you land.
Source: Ookla Speedtest Global Index · measured June 2026
Must-see
Nearby day trips
Say a few words
American English — local usage
- HelloHey / How are you doing?
- The bill, pleaseCan we get the check?
- To go, not eaten inTo go
- Fizzy drinkSoda
4 more phrases
- The undergroundThe subway
- QueueLine
- Ground floorFirst floor
- Thank you very muchThanks so much
Religion
Christian majority, no state religion
Constitutionally separated from the state, and enormously varied by region — the south is far more observant than the coasts.
Do's and don'ts
Do
- Tip 18-20% at restaurants and bars — servers are paid below minimum wage and depend on it
- Expect sales tax to be added at the till, not shown on the shelf price
- Make small talk with strangers; friendliness is genuine and not a prelude to anything
- Carry ID if you look under about 35 and intend to drink
Don't
- Do not skip the tip to make a point — take it up with the manager instead
- Do not discuss politics, guns or healthcare with strangers unless invited
- Do not stand too close; personal space is larger than in Europe or Latin America
- Do not joke about security at airports or borders
Where to stay in Chicago
No Holistay rentals in Chicago yet — the platform is just opening up. Every listing here will have a video tour and the option to negotiate the nightly price directly with the host.
In the meantime, here is Chicago on the sites that do have the inventory — each search is already filled in:
- Booking.com hotels, guesthouses and apartments — the widest coverage almost everywhere
- Airbnb whole homes and apartments, and the better option for a week or more
How to get there
Fly into O’Hare ORD
45 minfrom the airport· 25 km as the crow flies
45 min on the Blue Line, which runs all night.
Also worth pricing: Midway MDW — 30 min on the Orange Line, and mostly domestic.
Google Flights · Rome2Rio for the trains, buses and ferries as well as the flights
