Weekend getaways from Chicago

55 weekend-ready destinations depart from Chicago right now, 54 of them direct. The cheapest fare is €41 to Baltimore — all options on this page take under 3 hours each way, leaving enough time for a full Friday-to-Sunday break. Fares are updated regularly; prices shown are the lowest observed this week.

Best weekend getaways from Chicago right now

Looking for a quick weekend escape from Chicago? These destinations combine short flight times, current low fares, and enough flexibility for a two- or three-day trip. The cheapest option in this list is Baltimore from €41.

Baltimore
United States - 2h 7m - Direct
from €41
Philadelphia
United States - 2h 23m - Direct
from €57
Atlanta
United States - 2h 22m - Direct
from €68
Memphis
United States - 1h 58m - Direct
from €70
Minneapolis
United States - 1h 46m - Direct
from €72

Why these destinations?

- Short flight time from the origin airport
- Low current fares compared with nearby destinations
- Practical for a 2-3 day city break or short escape

5 of 5 top options have direct flights available - no connections needed for your weekend.

Booking tip: Saturday-morning departure + Monday-morning return is typically 20-30% cheaper than the popular Friday-evening out, Sunday-evening back pattern.

Prices refresh every 48-72 hours.

Cheapest destinations from Chicago

Showing the 30 cheapest destinations. Open the map for the full list.

Weekend getaways from other cities

Frequently asked questions

What's a good weekend trip from Chicago?

Right now the cheapest weekend-ready fare from Chicago is €41 to Baltimore, about 2 hours each way. That leaves plenty of time for two full days at your destination even on a Friday-to-Sunday schedule. See the full list above for all 55 options under 3 hours, covering 2 countries.

How many direct flights from Chicago work for a weekend?

54 of the short-haul destinations from Chicago currently have direct fares available. Direct is almost always the right call for a 2-night break — you land fresher, skip the connection stress, and save time on both ends of the trip. If a direct option is even €20 more than a connecting flight, it's usually worth it for a trip this short.

When should I book a weekend flight from Chicago?

4-6 weeks ahead usually gets you the best combination of price and seat availability. Friday-evening departures and Sunday-evening returns are the most popular, so they cost more — Saturday-morning outbound and Monday-morning return is often 20-30% cheaper for the same destination. Last-minute deals do appear (within 14 days), but you're at the mercy of what's left.

What counts as "short-haul" from Chicago?

We filter to flights under 3 hours one-way. That threshold is based on a practical test: a 3-hour flight allows you to leave Chicago on a Friday evening after work and arrive in time for dinner at your destination — leaving the full Saturday and Sunday free. Flights longer than 3 hours start to eat meaningfully into a 2-night break.