How to find cheap flights to to Chicago?
This guide covers everything you need to know about finding budget-friendly flights to Chicago’s main airports—O’Hare International (ORD) and Midway International (MDW). Expect airline hacks, booking windows, flight deals, nonstop route pricing, baggage-fee tips, credit-card strategies, airport notes, last-minute tactics, and travel-insurance guidance.
🕒 Best Times to Book Flights to Chicago
Late-night and early-morning departures usually deliver the best value for ORD-bound flights.
📉 Cheapest Month to Fly to Chicago
January, February, and October typically bring the lowest fares into Chicago. Roundtrip tickets often drop 20–35% compared to peak holiday and summer travel.
✈️ Nonstop Flights to Chicago — Airlines + Prices
Typical roundtrip price ranges for common nonstop routes into ORD/MDW:
| Route | Airlines | Typical Price |
|---|---|---|
| LAX → ORD | United, American, Delta | $138–$268 |
| DFW → ORD | American, United | $112–$229 |
| ATL → MDW/ORD | Delta, Southwest | $119–$238 |
| DEN → ORD | United, Southwest | $98–$188 |
| PHX → ORD | American, United | $129–$249 |
🔥 Flight Deals to Chicago
- LAX → ORD: from ~$142 one-way
- DFW → ORD: from ~$118 one-way
- ATL → MDW: from ~$126 one-way
- DEN → ORD: from ~$94 one-way
Track deal drops via Google Flights or Kayak.
🛫 Airport Guide: ORD vs MDW
ORD — O’Hare International Airport
- Major hub with extensive lounges and dining options.
- Allow extra time for terminal transfers due to airport size.
- Consistently more nonstop options than MDW.
MDW — Chicago Midway Airport
- Smaller footprint = shorter security lines.
- Southwest-dominant airport with frequent domestic deals.
- Easy access to downtown Chicago.
💳 Credit Card Travel Tips
- Use cards with boosted airfare earnings (Amex, Chase premium tiers).
- Redeem miles for ORD routes — often better availability than MDW.
- Free-checked-bag perks save $30–$35 per direction on most carriers.
⏳ Last-Minute Flights to Chicago
If traveling within 72 hours, check award availability first — United and American occasionally release last-minute saver space for ORD.
- Consider nearby airports (MKE) if prices spike.
- Try multi-city searches or flexible return dates.
🛡️ Travel Insurance
Weather delays are common in Chicago winters. Look for plans covering trip interruption, delay reimbursement, and baggage protection.
🧳 Baggage Fees
- United: $30–$35 first checked bag
- American: $30–$35
- Delta: $30–$35
- Southwest: Two free checked bags
💵 Price Examples (Roundtrip Estimates)
| Origin | Typical Roundtrip |
|---|---|
| LAX → ORD | $138–$268 |
| DFW → ORD | $112–$229 |
| DEN → ORD | $98–$188 |
| PHX → ORD | $129–$249 |
✅ Final Tips
- Compare ORD vs MDW — savings vary weekly.
- Search flexible-date calendars.
- Use airline rewards + credit card perks to cut total trip cost.
- Book midweek for better fares.