Boston trip from Chicago Midway (MDW): what 4 nights cost
For 2 travelers, a 4-night Boston trip from Chicago Midway (MDW) runs about $1,926 to $2,596 with the round-trip flight, hotel, food and things to do. Here are three ways to spend it.
Plan it with my dates and budgetThree plans
| Plan | Flight | Hotel | Flight | Hotel | Food | Things to do | Total |
|---|---|---|---|---|---|---|---|
| Best trip | JetBlue non-stop | Hyatt Regency Boston · 4★ | $470 | $1,120 | $768 | $238 | $2,596 |
| Best value | JetBlue non-stop | HI Boston, private room · 2★ | $470 | $480 | $768 | $238 | $1,956 |
| Least cash | Southwest non-stop | HI Boston, private room · 2★ | $440 | $480 | $768 | $238 | $1,926 |
Best trip skips budget airlines, Basic Economy and hostels. Best value and Least cash may use them to save money.
The Best trip, day by day
Day 1
- Freedom Trail walkfree
- Quincy Market chowderOrder: New England clam chowder in a bread bowl · in your food budget
Day 2
- North End food walk$110 for 2
- Union Oyster HouseOrder: Raw oysters and clam chowder · in your food budget
Day 3
- Harvard Yard and Cambridgefree
- OleanaOrder: Baked Alaska with coconut ice cream · $34 for 2 over your food budget
Day 4
- Tea Party Ships museum$70 for 2
- Neptune OysterOrder: Hot lobster roll with butter · $24 for 2 over your food budget
Flights from Chicago Midway (MDW)
Round trip for 2.
| Airline | Stops | Time each way | Price |
|---|---|---|---|
| United Basic Economy via Newark | 1 stop | 4h 44m | $350 |
| American via Philadelphia | 1 stop | 4h 48m | $410 |
| United via Newark | 1 stop | 4h 44m | $430 |
| Southwest non-stop | non-stop | 2h 23m | $440 |
| JetBlue non-stop | non-stop | 2h 23m | $470 |
| Delta non-stop | non-stop | 2h 23m | $490 |
Food: about $96 a person a day
Breakfast$16
Lunch$22
Dinner$48
Snacks and coffee$10
Restaurants worth the trip
- Neptune OysterOrder: Hot lobster roll with butter · about $60 a person
- Union Oyster HouseOrder: Raw oysters and clam chowder · about $45 a person
- Mike's Pastry cannoliOrder: Ricotta cannoli · about $6 a person
- Quincy Market chowderOrder: New England clam chowder in a bread bowl · about $15 a person
- OleanaOrder: Baked Alaska with coconut ice cream · about $65 a person
Questions
How much is a 4-night trip to Boston from Chicago Midway (MDW)?
About $1,926 to $2,596 for 2 travelers, including the round-trip flight, 4 nights of hotel, food and things to do.
What's the cheapest flight from Chicago Midway (MDW) to Boston?
United Basic Economy via Newark at about $350 round trip for 2.
How much should I budget for food in Boston?
About $96 a person a day at mid-range places, or $768 for 2 over 4 days.
More from Chicago Midway (MDW)
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Change the dates, budget, travelers and how you eat, or add your points and miles.
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