What's the cheapest weekend trip from Chicago?

Baltimore currently shows the lowest real fare on file among Chicago's short-haul routes, at €40.

Why isn't every destination from Chicago listed here?

This page only includes routes with a real flight time of 2.5 hours or under — long enough to actually get somewhere, short enough to fit a real weekend. Longer routes are on our full "flights from Chicago" page instead.

How many routes did you check?

We checked up to 40 real short-haul routes from Chicago and found 14 with a live fare on file.

What's the best time to fly for a weekend trip?

A Friday evening or Saturday morning departure with a Sunday evening return is the classic pattern — check the live fare calendar on each route's own page for the cheapest specific dates.

Do these fares include baggage?

Not necessarily — for a short weekend trip, cabin baggage only often works out cheapest. Check each airline's allowance before booking.

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Best Weekend Trips from Chicago

Real short-haul destinations from Chicago — 2.5h flight time or under — ranked by flight time, with real live fares. Not every destination from Chicago fits a weekend; this page only shows the ones that do.

Real weekend-trip destinations

Destination	Flight time	Fare
Detroit	56m	€96
Minneapolis	1h 07m	€57
Toronto	1h 19m	€105
Washington	1h 36m	€79
Atlanta	1h 38m	€60
Ottawa	1h 44m	€212
Philadelphia	1h 46m	€85
Montreal	1h 54m	€132
Baltimore	1h 55m	€40
Dallas	2h 01m	€91
Boston	2h 08m	€96
Denver	2h 10m	€58
Houston	2h 15m	€40
Orlando	2h 24m	€66

Making the most of a weekend trip

Pack cabin baggage only where you can — it's usually enough for 2-3 nights and skips checked-bag fees.
A Friday evening or Saturday morning departure with a Sunday evening return is the classic weekend pattern.
Book accommodation close to the centre — a short trip loses real time to a long transfer each way.
Check each route's own page for a full fare calendar before settling on exact dates.
Have a backup destination from the list above — the cheapest option can shift by the time you book.

Continue planning your trip to Detroit

Same destination, real availability — no need to search again.

Flights to Detroit Hotels in Detroit Things to do in Detroit Rent a car

Continue planning your trip to Minneapolis

Same destination, real availability — no need to search again.

Flights to Minneapolis Hotels in Minneapolis Things to do in Minneapolis Rent a car

Continue planning your trip to Toronto

Same destination, real availability — no need to search again.

Flights to Toronto Hotels in Toronto Things to do in Toronto Rent a car

More from Chicago

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FAQs — Weekend trips from Chicago

Detroit has the shortest real flight time from Chicago among the routes we checked, at around 0h 56m.