Which hotel is recommended for this trip?

This plan recommends the Hilton Club The Quin New York, specifically a two-bedroom suite that sleeps five, for its location and ability to accommodate the group together.

Which Broadway show is included in this itinerary?

The itinerary includes tickets to Hadestown at the Walter Kerr Theatre. It's recommended to purchase five adjacent seats as soon as the performance calendar opens.

Where can we experience live jazz music?

You will attend a late set at the Village Vanguard in Greenwich Village. Buy all five tickets in one transaction and arrive about 45 minutes before the set to be seated together.

What is the recommended transportation around the city?

The plan primarily uses walking and the subway for getting around the city. For airport transfers, one yellow-taxi minivan or UberXL is recommended for the group and luggage.

Where will we have our celebration dinner?

The celebration dinner is planned for Ci Siamo. Reservations generally release about 28 days in advance, and booking immediately for a table for five is advised.

Midtown Manhattan skyscrapers at sunrise with the Empire State Building in golden light

Sample itinerary · 3 days

3-Day New York Girls' Weekend Itinerary

Five of you, one weekend, and nobody waiting on the group to decide.

Going to: New York City, New York
Length: 3 days
Travelers: Friend groups
Trip total: $4,840–$7,335

$4,840–$7,335

The total covers flights from Chicago, Illinois, lodging, getting around and tickets and tours for the whole party, plus food, gas and parking estimated in the breakdown below.

Things to do

Vintage hunt at City Opera Thrift Shop (Day 1)
Late set at the Village Vanguard (Day 1)
Cocktails at Dante West Village (Day 1)
The Metropolitan Museum of Art and Cantor Roof Garden (Day 2)
Luxury resale at The RealReal Madison Avenue (Day 2)
Hadestown at the Walter Kerr Theatre (Day 2)
Post-show cocktails at Pebble Bar (Day 2)
Grand Central Terminal Main Concourse (Day 3)

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Why this plan works

The arrival day stays deliberately light: after settling into Midtown, the group heads south once for vintage shopping, a reserved shared-plate dinner and a Village jazz set. The evening remains geographically compact and honors the requested late-night celebration style without exceeding two real activities.

Open the Breakfast en route to O'Hare leg in Maps Open the Vintage hunt at City Opera Thrift Shop leg in Maps

5:45 AM
Breakfast en route to O'Hare
5:45 AM
This accounts for breakfast without adding a first-day stop in the starting city.
Grab breakfast on the way to the airport rather than making a separate stop in Chicago; allow enough time to reach the terminal by 6:15 AM.
8:15 AM–11:30 AM
Typical departure · ORD → LGA
8:15 AM–11:30 AM
A morning nonstop preserves Friday afternoon while avoiding an unnecessarily early pre-dawn departure.
Operating airline: American, Delta or United; realistic departure around 8:15 AM from ORD and arrival around 11:30 AM at LGA; nonstop, typically about 2 hours 15 minutes in the air; arrive at ORD 2 hours before departure. Confirm the operating terminal when schedules are published.
11:30 AM–12:45 PM
LaGuardia to Midtown in one large vehicle
11:30 AM–12:45 PM
One appropriately sized vehicle prevents the party from splitting and is simpler than changing from the airport bus to the subway with luggage.
Collect luggage, then use the official taxi line for a minivan or request one UberXL that carries all five adults and their bags. Allow 45–70 minutes depending on Friday traffic.
12:45 PM–1:15 PM
Hilton Club The Quin New York
12:45 PM–1:15 PM
The chain hotel is in a walkable Midtown neighborhood near Central Park and subway lines. A two-bedroom suite with a king bedroom, a second king or two-double bedroom configuration and a living-room sleeper sofa keeps five friends together under one booking rather than scattering rooms across floors.
Leave bags if the suite is not ready, then request written confirmation that the two-bedroom suite allocation accommodates all five on one floor. The stay runs through Sunday checkout.
1:30 PM–2:30 PM
Lunch at Urban Hawker
1:30 PM–2:30 PM
Counter service is flexible if the flight arrives late, and the food hall can accommodate five without a reservation.
Walk about 10 minutes to this Singaporean food hall and order independently from stalls such as Hainan Jones or Padi; regroup at one table. The variety suits adventurous eaters without forcing a long arrival-day meal.
2:30 PM–3:15 PM
Subway · Urban Hawker → City Opera Thrift Shop
2:30 PM–3:15 PM
This leg connects the two planned stops without adding another attraction.
Take the subway from Urban Hawker to City Opera Thrift Shop, allowing this interval for station access and the ride.
3:15 PM–4:45 PM
Vintage hunt at City Opera Thrift Shop
3:15 PM–4:45 PM
This is a genuine vintage stop with a changing donated inventory, directly covering the group's shopping-and-vintage request.
Browse the West 26th Street store for vintage clothing, accessories, art and housewares. Ninety minutes provides room to shop without squeezing the Friday schedule.
4:45 PM–5:20 PM
Hotel reset or unhurried Chelsea break
4:45 PM–5:20 PM
A real pause keeps the arrival day moderate before dinner and late-night music.
Take the subway uptown to the hotel for a short reset, or remain in Chelsea and rest before dinner. If returning to the hotel, allow about 25 minutes each way and leave again by 5:20 PM.
6:00 PM–7:45 PM
Celebration dinner at Ci Siamo
6:00 PM–7:45 PM
The menu is built for shared ordering, the room handles a five-person table properly, and this is the one dinner worth reserving well ahead.
Book ahead · Call ahead: most restaurants open tables about a month out, and large parties often need longer
Share seasonal vegetables, handmade pastas and wood-fired mains at a table for five. Ask how far ahead reservations open and set a reminder for that morning, then book the Friday table for five as soon as the calendar opens.
7:45 PM–8:35 PM
Walk · Ci Siamo → Village Vanguard
7:45 PM–8:35 PM
This leg connects the two planned stops without adding another attraction.
Walk from Ci Siamo to Village Vanguard, keeping this interval for the journey rather than another visit.
9:00 PM–10:20 PM
Late set at the Village Vanguard
9:00 PM–10:20 PM
This supplies the requested live music at one of New York's defining jazz rooms and suits the group's out-late style.
Book ahead · Timed-entry tickets usually release a month or two ahead; confirm with the venue
Hear a full jazz set in the historic basement club. Purchase all five tickets together when the October calendar is published; seating is close and capacity is limited, so arrive approximately 45 minutes before showtime and expect a one-drink minimum per person if current policy retains it.
10:30 PM–11:45 PM
Cocktails at Dante West Village
10:30 PM–11:45 PM
The bar extends the celebration with serious cocktails while remaining within walking distance of the jazz club.
Book ahead · Call ahead: most restaurants open tables about a month out, and large parties often need longer
Walk about 10 minutes for negronis, martinis and alcohol-free options. Reserve a table for five if offered for the selected date; five adjacent walk-in bar seats are unlikely on Friday night.
11:45 PM–12:20 AM
Taxi · Dante West Village → Hilton Club The Quin New York
11:45 PM–12:20 AM
A late-night taxi gets you back without another long walk.
Take a taxi from Dante West Village to Hilton Club The Quin New York. A door-to-door ride keeps the late return straightforward after the evening out.

If you fall behind

What to cut if you fall behind: skip City Opera Thrift Shop and protect the reserved dinner and Village Vanguard set.

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Bookings & costs

$4,840–$7,335

0 of 12 bookable items booked

Food not included: about $2,700, listed below

0 of 12 bookable items booked

Locked in

paid or reserved

Still to book

$5,790

est. $4,600–$6,975 · 12 items

Gas & parking

$300

est. $240–$360

Booked prices are exact. Everything else is an estimate.

Know before you go

Practical notes for this trip — the things worth sorting before you leave.

Booking windows & timing

Book the Hilton Club The Quin first and obtain written confirmation that the selected two-bedroom suite sleeps five. If booking separate room components rather than the named suite, same-floor placement is only a request and does not meet this plan's lodging requirement.
Time-sensitiveCheck in · Hilton Club The Quin New York
Purchase five adjacent Hadestown seats as soon as the October performance calendar opens. Friday and Saturday evening performances can become expensive well before the trip.
Time-sensitiveHadestown at the Walter Kerr Theatre
The Village Vanguard is a small room, so check its current ticketing and seating rules for a party of five — seats may be assigned on arrival rather than chosen. Buy all five tickets in one transaction when the October calendar is posted, then arrive about 45 minutes before the set so the group can be seated together.
Time-sensitiveLate set at the Village Vanguard
Ask Ci Siamo how far ahead it opens reservations and set a reminder for that morning, then reserve a table for five as soon as the calendar opens. Bar seating is unlikely to keep five friends together on a Friday evening.
Time-sensitiveCelebration dinner at Ci Siamo

Set up before you go

Add one contactless payment card to each traveler's phone before departure. OMNY works directly at subway turnstiles, so the group does not need MetroCards or a shared transit account.

Getting around & driving

For five adults with luggage, take one yellow-taxi minivan or UberXL from LaGuardia rather than relying on a standard car. During the rest of the weekend, subway rides avoid Midtown gridlock and every routing block keeps the group together.
LaGuardia to Midtown in one large vehicle

Weather & packing

Early October can alternate between mild afternoons and chilly evenings, and the Met rooftop may close for rain or high wind. Bring a compact rain layer and check rooftop access with the museum on the morning of the visit.
The Metropolitan Museum of Art and Cantor Roof Garden

Crowds & timing

Enter the Met at opening and use the Fifth Avenue entrance before tour groups build. Broadway security and Village Vanguard seating also reward arriving at the stated times rather than cutting transfers close.

Money

Cards and contactless payment are accepted nearly everywhere on this itinerary. Budget roughly 20% for table-service tips, while counter-service tipping is optional and can be adjusted on the screen.

Want this trip on your dates?

Make this yours — free, no account, no card.

Plan a trip like this

Questions about this plan

Which hotel is recommended for this trip?: This plan recommends the Hilton Club The Quin New York, specifically a two-bedroom suite that sleeps five, for its location and ability to accommodate the group together.
Which Broadway show is included in this itinerary?: The itinerary includes tickets to Hadestown at the Walter Kerr Theatre. It's recommended to purchase five adjacent seats as soon as the performance calendar opens.
Where can we experience live jazz music?: You will attend a late set at the Village Vanguard in Greenwich Village. Buy all five tickets in one transaction and arrive about 45 minutes before the set to be seated together.
What is the recommended transportation around the city?: The plan primarily uses walking and the subway for getting around the city. For airport transfers, one yellow-taxi minivan or UberXL is recommended for the group and luggage.
Where will we have our celebration dinner?: The celebration dinner is planned for Ci Siamo. Reservations generally release about 28 days in advance, and booking immediately for a table for five is advised.