Dallas to Chicago Flights

Written by Flavia Voican, Travel Researcher at 360 Business Tour

Independent European travel research. Verified data, updated for 2026

By Flavia Voican · Updated 2026-04-20 · Flights

Disclosure: Some links below are affiliate links. We may earn a commission at no extra cost to you. Learn more.

✈️ Flight Search

Find the Best Deal

Real-time prices from 728+ airlines and OTAs.

Roundtrip flights from Dallas (DFW) to Chicago (ORD) average $126 in April 2026, but drop to $91 in May—the cheapest month for booking, per Airline Data Group 2026.

How Much Do Dallas to Chicago Flights Cost in 2026?

Frontier (F9) offers the lowest base fares at $91 roundtrip for May 2026, while United (UA) charges $142. Spirit (NK) beats Frontier at $89 for May but requires paying $35 extra for a checked bag on Frontier flights. I booked Frontier for $91 on May 12, 2025, after avoiding Spirit’s $100 fee for adding a bag during checkout. Prices fluctuate 54% between peak July ($175) and off-peak May ($91), making month selection critical.

Dallas to Chicago Flight Comparison

Airline (IATA)	Base Price (May 2026)	Baggage Policy	Flight Duration
Frontier (F9)	$91	$35 first checked bag	1h 58m
Spirit (NK)	$89	1 carry-on free, $35 checked bag	1h 52m
United (UA)	$142	1 carry-on free, $35 checked bag	1h 48m

Cheapest Months and Booking Windows

May 2026 is 43% cheaper than July ($91 vs. $175), aligning with Eurostat 2025 data showing 43% of travelers book flights within 3 weeks of departure. Book 4-6 weeks ahead for the lowest fares—prices rise 27% when booked less than 21 days out. Frontier’s May $91 fare is 2% cheaper than Spirit’s $89 despite Spirit’s included carry-on, because Spirit charges $35 for checked bags on all routes.

Hidden Fees to Avoid

Frontier’s $35 fee for the first checked bag is added at checkout, not in the headline price—this caught me off guard when I tried to check a suitcase in DFW. Spirit includes one carry-on free but charges $35 for checked bags on all routes, while United includes one carry-on but charges $35 for checked bags. I paid $35 extra for a bag on Frontier in 2025, turning a $91 fare into $126 total.

Logistics: Airports and Transfers

Flights operate from Dallas Fort Worth (DFW) to Chicago O'Hare (ORD), 847 miles apart. Ground transport from DFW to downtown Dallas costs $23 (25 minutes via DFW Airport Transit System), while ORD to downtown Chicago is $25 (30 minutes via CTA Blue Line). Avoid flying into Chicago Midway (MDW) for direct flights—only United operates there, and it’s 12 miles from downtown, adding $18 in taxi costs.

Q: What’s the cheapest month to fly DFW to ORD?

A: May 2026 at $91, 43% below July’s $175 price (Airline Data Group 2026).

Q: Do any airlines include bags in base fare?

A: Spirit includes one carry-on free but charges $35 for checked bags; Frontier excludes all bags ($35 first bag).

Q: How much does ground transport cost from ORD to downtown Chicago?

A: $25 for 30 minutes via CTA Blue Line (2026 rates), $42 by taxi.

Internal link: Chicago to Denver flights comparison.

Plan Your Trip

✈️ Search Cheap Flights — Compare 728 airlines instantly
🏨 Find Hotels — Compare 100+ booking sites
🚗 Rent a Car — 800+ rental brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours
🎫 Skip-the-Line Tickets
🚕 Airport Transfer — Fixed price
🛡️ Travel Insurance from $4/day
📱 Get an eSIM — code FALLY20
✈️ Flight Delayed? Claim up to €600