Illinois · packages from $269
Chicago travel guide
Architecture on the river, lakefront summers and deep-dish nights
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Overview
Chicago is a compact, transit-friendly city with a world-class architecture story, a serious food scene and 26 miles of lakefront path.
Summer festivals and boat cruises are the highlight; winter brings lower rates, holiday markets and museum days.
Things to do
Top attractions in Chicago
Architecture river cruise
The single best introduction to the city — book ahead in summer.
Millennium Park
The Bean, Pritzker Pavilion concerts and seasonal ice skating.
Art Institute of Chicago
One of the finest collections in the country.
Willis Tower Skydeck & 360 Chicago
Glass-ledge views over the lake and the grid.
Navy Pier
Wheel rides, cruises and summer fireworks.
Wrigleyville & neighbourhood nights
Ballgames, comedy clubs and live music.
Where to stay
Hotel & accommodation highlights
The Loop
Central for museums, theatre and transit.
River North
Dining and nightlife within walking distance.
Magnificent Mile
Shopping-first stays close to the lake.
Lincoln Park
Leafy, residential and family-friendly.
Getting there
Flight information
- Airports
- O'Hare (ORD), Midway (MDW)
- Best value season
- January to March, early November
- Airport transfer
- Blue Line and Orange Line trains, or private car
- Typical fares
- Round trips from $149 outside summer peak
Tours & activities
Guided experiences in Chicago
- Architecture and skyline river cruises
- Guided food tours including deep-dish tastings
- Museum campus combination passes
- Neighbourhood walking tours in Pilsen and Wicker Park
- Lakefront bike rentals and guided rides
Good to know
Travel tips
- Lake winds make winter feel colder than the forecast — pack layers.
- The CTA gets you almost everywhere; a hire car is rarely needed.
- Reserve architecture cruises and top restaurants weeks ahead in summer.
- Museum free days exist for Illinois residents; ask us for the calendar.
Call-in booking assistance for Chicago
Tell us your dates and party size and we will build your Chicago trip — flights, hotel, tours and transfers — on the call. Bookings are taken by phone only.
