Find the cheapest weekend away

Flights plus hotels with the real total, not the cheap-looking nightly rate, then what happens if you move one day.

1. 1

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   @Firecrawl Use Firecrawl Alexandria to find the cheapest Friday to Sunday trip to Chicago from New York, flights plus hotel, with total prices and cancellation terms. What changes if I leave Thursday night?

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   • Show me three destinations within a 3 hour flight of my city for under $400 total for two nights
   • Compare hotels under $200 a night with free cancellation and a guest rating above 8
3. 3

   What came back

   Claude Code (Claude Opus 5.5) sent back, word for word:

   The cheapest Fri–Sun trip is the weekend of Nov 13–15. The cheapest workable version is about $487 in a hostel dorm bed, or $594 with a private hotel room. Leaving Thursday night saves about $25 on the flight, but the extra hotel night costs more than that, so the trip ends up $38–$155 more expensive.

   I checked the next four weekends: Oct 23, Oct 30, Nov 6 and Nov 13. Prices are for 1 adult, economy, any NYC airport to Chicago, as of today (Oct 20). Flights come from Google Flights and hotels from Booking.com, both through Alexandria. All hotel totals include taxes and fees.

   Cheapest weekend by flight price (Fri→Sun round trip, starting fares)

   Weekend	Cheapest nonstop	Cheapest hostel (2 nights)
   Oct 23–25	$375	$114 + tax
   Oct 30–Nov 1	$365	$92 + tax
   Nov 6–8	$347	$92 + tax
   Nov 13–15	$243	$87 + tax

   Catch: the $243 fare only works with a 5:00 AM Sunday return. A normal Sunday return costs more: $355 on Southwest, coming back at 5:15 PM, or $360 on American, coming back after 2:30 PM.

   Fri Nov 13 → Sun Nov 15 packages

   Flight for all three: Southwest LGA 3:05 PM → Midway 4:45 PM, back Sunday Midway 5:15 PM → LGA 8:20 PM, $355 round trip, carry-on included, no checked bag.

   Stay	Hotel total	Trip total	Cancellation
   HI Chicago Hostel, dorm bed (8.5 rating, downtown)	$132	$487	Free until Nov 11; after that you pay the first night. Nothing to pay until you arrive. A non-refundable rate is $119, for a $474 trip.
   Gateway Inn Oak Lawn, private queen room (7.2 rating, near Midway, 12.6 mi from downtown)	$239	$594	Free until Nov 12; after that you pay the first night. Charged in advance.
   Holiday Inn Chicago Midway, king room (7.5 rating)	$362	$717	Free until Nov 6; after that you pay the first night. Nothing to pay until you arrive.

   If you can take the 5 AM Sunday flight, the dorm version drops to about $362.

   If you leave Thursday night (Nov 12 → Nov 15)

   • Flight: American LGA 9:20 PM → O'Hare 11:09 PM, with a Sunday afternoon or evening return (2:31–8:00 PM), costs $330. That's $25 less than Friday. United also has a 9:30 PM flight from LGA, but I didn't price its return.
   • Hotel: you pay a 3rd night.
     • Hostel dorm: $195 → $525 total (+$38 vs. Friday)
     • Gateway Inn: $347 → $677 (+$83)
     • Holiday Inn: $542 → $872 (+$155)
   • Logistics: you land at O'Hare after 11 PM. The downtown hostel is a straight ride on the Blue Line train. The two Midway-area hotels are about 25 miles from O'Hare, so that first night costs you a late taxi or rideshare on top of the room.
   • Cancellation deadlines move a day earlier: hostel free until Nov 10, Gateway Inn until Nov 11, Holiday Inn until Nov 5.

   Notes

   • Flight cancellation terms weren't in the data. Any US flight booked at least 7 days before departure can be cancelled free within 24 hours of booking. After that it depends on fare type: Basic Economy usually can't be changed. Check the fare type before you pay.
   • Starting fares on the other weekends assume the cheapest return, which may also be an early-morning flight.
   • Prices change quickly; Southwest and the hostel had the fewest seats/beds left.

   My pick is Friday Nov 13 with the Gateway Inn ($594). It pairs well with Southwest's Midway flights and gives you a private room you can cancel free until the day before, though you're charged up front. Leave Thursday night only if the extra evening in Chicago is worth $38–$155 to you.

   Sources usedGoogle FlightsBooking.com125 credits · Oct 20, 2026