Tripfitly
Dallas-Fort Worth (DFW) → Chicago

Chicago trip from Dallas-Fort Worth (DFW): what 4 nights cost

For 2 travelers, a 4-night Chicago trip from Dallas-Fort Worth (DFW) runs about $1,694 to $2,094 with the round-trip flight, hotel, food and things to do. Here are three ways to spend it.

Plan it with my dates and budget

Three plans

PlanFlightHotelFlightHotelFoodThings to doTotal
Best tripSouthwest non-stopHyatt Regency Chicago · 4★$400$800$720$174$2,094
Best valueSouthwest non-stopWicker Park boutique hotel · 3★$400$680$720$174$1,974
Least cashSouthwest non-stopLoop hostel, private room · 2★$400$400$720$174$1,694

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 Dallas-Fort Worth (DFW)

Round trip for 2.

AirlineStopsTime each wayPrice
Southwest non-stopnon-stop2h 16m$400
United non-stopnon-stop2h 16m$440
American non-stopnon-stop2h 16m$460

Food: about $90 a person a day

Breakfast$15
Lunch$20
Dinner$45
Snacks and coffee$10

Restaurants worth the trip

Questions

How much is a 4-night trip to Chicago from Dallas-Fort Worth (DFW)?

About $1,694 to $2,094 for 2 travelers, including the round-trip flight, 4 nights of hotel, food and things to do.

What's the cheapest flight from Dallas-Fort Worth (DFW) to Chicago?

Southwest non-stop at about $400 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 Dallas-Fort Worth (DFW)

Chicago costs from every airport

Make it yours

Change the dates, budget, travelers and how you eat, or add your points and miles.

Plan my trip