Dallas to Chicago: Cheap Flights & Deal Alerts
Dallas to Chicago is a highly competitive route with excellent deal potential. Round-trip fares typically range $180-300, with Southwest and American offering frequent service. Both O'Hare and Midway provide different advantages for savvy travelers.
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Good Price Range for DFW → Chicago
Excellent Deal
Under $150
Book immediately during sales
Good Value
$150-250
Solid pricing year-round
Average
$250-300
Peak season and busy periods
Cheapest Months & Days to Fly from Dallas
Best Months
- • January-February: Coldest weather, lowest demand
- • Late February-March: Before spring business picks up
- • September-October: After summer tourism ends
- • Early December: Before holiday travel surge
Best Days
- • Tuesday/Wednesday: Mid-week departures save 20%+
- • Saturday departures: Lower business travel
- • Avoid Monday/Friday: Business travel premium
- • Early morning/late night: Less convenient = cheaper
Airlines & Airports (DFW vs DAL when relevant)
From DFW International:
American Airlines
Hub advantage with hourly flights to O'Hare
Best for: Frequent schedules, upgrades
United Airlines
O'Hare hub with good connectivity
Best for: International connections
From Dallas Love Field:
Southwest Airlines
Multiple daily flights to Midway (MDW)
Best for: Free bags, no change fees, Companion Pass
Airport Strategy:
- • O'Hare (ORD): More airlines, better connections, but farther from downtown
- • Midway (MDW): Southwest focus, closer to city center, often cheaper
- • Pro tip: Check both airports - sometimes Southwest undercuts others by $50+
How to Snag Mistake Fares
Dallas-Chicago sees frequent fare wars and mistake pricing:
- 1Southwest vs American battles: When one drops prices, the other matches within hours
- 2Winter flash sales: Airlines clear capacity during slow Chicago months
- 3System glitches: Look for sub-$120 roundtrips (extremely rare but happens)
- 4End-of-quarter pushes: Airlines discount to hit revenue targets
Recent Deals We've Seen
Examples of great Dallas-Chicago deals (prices expired):
- • Southwest winter sale: Dallas Love Field to Midway in the $120s
- • American hub pricing error: DFW to O'Hare under $100 roundtrip
- • United end-of-year clearance: Last-minute fares around $140
- • Multi-airline competition: Spring fares dropping to $130 range
Note: These are examples of deal types we track. Actual prices vary by date and availability.
FAQs
What's a good price for Dallas to Chicago flights?
Round-trip flights typically range $180-300. Great deals under $150 appear during airline sales and off-peak periods.
Which airlines fly from Dallas to Chicago?
American Airlines, Southwest, United, and Delta offer frequent service from DFW/DAL to Chicago O'Hare (ORD) and Midway (MDW).
Which Chicago airport should I choose?
O'Hare (ORD) has more flight options and is better for connections. Midway (MDW) is often cheaper with Southwest and closer to downtown Chicago.
Don't Just Plan Smarter. Fly Cheaper.
This route sees frequent fare wars. The traveler who gets alerted first gets the deal.
Free subscribers:
Weekly summaries (often after deals end)
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Instant alerts when Dallas-Chicago fares drop