Midwest / Illinois
Chicago
The long-haul US break Brits keep overlooking: base in River North or the Loop, ride the 'L' Blue Line in from O'Hare, do the river architecture cruise first, and aim for late spring or September.
Best length
3-4 nights, or longer paired with a wider US trip
Airport
O'Hare (ORD), ~27km northwest; Midway (MDW) closer for some US flights
Airport to centre
Blue Line 'L' ~45 min, about $5 paying per ride
Best base
River North or the Loop for first-timers
In short
Chicago at a glance
Chicago is the long-haul US city break that Brits keep overlooking: a proper working city on a Great Lake, with the best architecture tour in America, deep-dish-versus-tavern food arguments, and direct flights from Heathrow. Base yourself in River North or the Loop, do the river cruise before anything else, and come in late spring or September when the lakefront is at its best.
The short version
- Stay in River North or the Loop for a first trip: walkable to the river, the lakefront parks and the 'L', with the widest hotel choice.
- Book the Chicago Architecture Center river cruise early — it is the single best way to understand the city and the one tour worth paying full price for.
- Take the CTA Blue Line 'L' in from O'Hare for about £4 rather than a £35-£50 cab; it runs into the Loop in roughly 45 minutes.
- Willis Tower Skydeck and the glass Ledge are fine, but the architecture cruise and a walk through Millennium Park tell you more for less.
- Late May to June and September are the sweet spot: warm lakefront days without the July humidity, the deep-freeze winter or peak summer hotel prices.
Chicago is the big American city Brits skip in favour of New York, and that is the case for going. It is a real working city built along a Great Lake, with the best urban architecture tour in the country, an Art Institute that rivals anything in Europe, and a deep-dish-versus-tavern-cut pizza argument you will be dragged into within a day. Heathrow flies direct to O’Hare in about eight and a half hours, and the city sits six hours behind the UK, so the first day is usually a jet-lagged half-day rather than a full one.
The structure of a good trip is simple: stay in River North or the Loop so you can walk to the river and the lakefront, book the Chicago Architecture Center river cruise before you do anything else, and use the ‘L’ rather than cabs. The Willis Tower Skydeck and its glass Ledge are a fun hour but not the point of the city; Millennium Park, the lakefront trail and the West Loop food scene are. Come in late spring or September and the lake works in your favour. Below, the structured planning — where to stay, what to book, the Blue Line in from O’Hare and a realistic budget in pounds — picks up from here.
One thing to plan for: US prices are quoted before tax and tip. The headline on a menu or hotel page is not what you pay, so build in roughly a fifth on top of restaurant bills and a city sales tax of about 10% on most spending before the trip feels expensive by surprise.
Keep a first trip focused: book the big timed sights, then leave room for neighbourhoods and food.
Top things to do in Chicago
Willis Tower Skydeck
Book a general-admission Skydeck ticket online with a timed slot rather than the expensive Fast Pass — at 412m up on the 103rd floor, the view is the same from either, and the standard ticket is roughly a third of the price. Go on a genuinely clear day: the whole point is seeing four states and the lakefront, and a grey Chicago sky turns the visit into a queue for a white-out. Allow an hour to 90 minutes, and aim for the first slot of the day or the last before sunset to beat the worst of the crowds at the glass Ledge boxes.
Millennium Park
Millennium Park is free, needs no ticket and is the first thing to do in the Loop on a clear day. Cloud Gate — the Bean — is the only stop you'll actually queue for, and even then only a few minutes for a clean reflection; the rest is a stroll. Come early morning for an empty Bean, or on a warm evening for the free Pritzker Pavilion concerts, and walk straight into the Art Institute next door to make a half-day of it.
Where to stay first
The areas that make a first visit easier — not an exhaustive directory.
River North
££ mid-rangeThe easiest first-timer base: walkable to the river cruise dock, the Mag Mile shops and the Loop, with the deepest pool of hotels at every price. Busy and a little corporate, but you waste no time getting anywhere.
Best for: First-timers, couples, short stays
The Loop
££ mid-rangeRight on top of Millennium Park, the Art Institute and the Skydeck, and the hub of the 'L' so the Blue Line drops you nearby from O'Hare. Quieter at night once offices empty, which suits a sightseeing-led trip.
Best for: Sightseeing-first trips, transport convenience
Gold Coast / Streeterville
£££ premiumThe upscale, lower-key alternative just north: leafier streets, the lakefront and Oak Street Beach on your doorstep, the same access to River North a little quieter. Expect to pay more for the calm.
Best for: Couples wanting calm, lakefront access, higher budgets
West Loop / Wicker Park
££ mid-rangeWhere Chicagoans actually go out — the best restaurants are in the West Loop and the most interesting bars around Wicker Park. Better for a longer stay or a repeat visit than a first three nights, as it is a 'L' ride from the main sights.
Best for: Food-led trips, repeat visitors, longer stays
Airport to city centre
| Option | Time | Cost | Book ahead? |
|---|---|---|---|
| CTA Blue Line 'L' from O'Hare to the Loop | ~45 min | about $5 (~£4) paying per ride at O'Hare | Best value; runs into the heart of downtown |
| CTA Orange Line 'L' from Midway to the Loop | ~25-30 min | about $2.75 (~£2.20) | Use if your US flight lands at Midway |
| Rideshare from O'Hare | ~30-50 min depending on traffic | usually $35-$55 (~£28-£44) plus airport fee | Good with luggage or late arrivals |
| Taxi from O'Hare | ~30-50 min | usually $45-$60 (~£36-£48) with tip | Simplest but the priciest option |
When to go
Sweet spot: Late May to June and September are the sweet spot: warm lakefront days, festivals and patio season without July-August humidity, peak hotel prices or the brutal winter wind.
Summer is the liveliest but most expensive and humid; book hotels and restaurants well ahead around festival weekends. Winter is genuinely cold — lake-effect wind and sub-zero temperatures from late November to March — so come for museums and indoor food rather than the lakefront. Spring and autumn give the best balance of weather and price.
What it costs
Direct UK return flights to O'Hare with British Airways or American from Heathrow are often £450-£700 in shoulder season when booked ahead; summer, Christmas and last-minute fares climb well past that. The flight is around 8.5 hours and there is a deep time-zone swing (six hours behind the UK).
Daily budget per person
US menu and hotel prices are pre-tax and pre-tip: budget for roughly 10.25% sales tax in the city plus 18-20% tipping on top of the headline figure, and expect a nightly hotel tax that pushes the room rate up further.
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