Chicago trip from Boston (BOS): what 4 nights cost
For 2 travelers, a 4-night Chicago trip from Boston (BOS) runs about $1,734 to $2,204 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 | Delta non-stop | Hyatt Regency Chicago · 4★ | $510 | $800 | $720 | $174 | $2,204 |
| Best value | JetBlue non-stop | Loop hostel, private room · 2★ | $460 | $400 | $720 | $174 | $1,754 |
| Least cash | Southwest non-stop | Loop hostel, private room · 2★ | $440 | $400 | $720 | $174 | $1,734 |
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
- Art Institute of Chicago$64 for 2
- Portillo's hot dogsOrder: Chicago-style hot dog and the chocolate cake · in your food budget
Day 2
- Field Museum$60 for 2
- Al's Italian beefOrder: Italian beef, dipped, with hot giardiniera · in your food budget
Day 3
- Girl & the GoatOrder: Wood-oven roasted pig face · $50 for 2 over your food budget
Day 4
- Lou Malnati's deep dishOrder: Deep dish with sausage on the buttercrust · in your food budget
Flights from Boston (BOS)
Round trip for 2.
| Airline | Stops | Time each way | Price |
|---|---|---|---|
| Southwest non-stop | non-stop | 2h 24m | $440 |
| United non-stop | non-stop | 2h 24m | $460 |
| JetBlue non-stop | non-stop | 2h 24m | $460 |
| American non-stop | non-stop | 2h 24m | $470 |
| Delta non-stop | non-stop | 2h 24m | $510 |
Food: about $90 a person a day
Breakfast$15
Lunch$20
Dinner$45
Snacks and coffee$10
Restaurants worth the trip
- Lou Malnati's deep dishOrder: Deep dish with sausage on the buttercrust · about $25 a person
- Portillo's hot dogsOrder: Chicago-style hot dog and the chocolate cake · about $12 a person
- AlineaOrder: The tasting menu, ending with the edible balloon · about $350 a person
- Al's Italian beefOrder: Italian beef, dipped, with hot giardiniera · about $12 a person
- Girl & the GoatOrder: Wood-oven roasted pig face · about $70 a person
Questions
How much is a 4-night trip to Chicago from Boston (BOS)?
About $1,734 to $2,204 for 2 travelers, including the round-trip flight, 4 nights of hotel, food and things to do.
What's the cheapest flight from Boston (BOS) to Chicago?
Southwest non-stop at about $440 round trip for 2.
How much should I budget for food in Chicago?
About $90 a person a day at mid-range places, or $720 for 2 over 4 days.
More from Boston (BOS)
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