Chicago Cheap Flights — Compare & Book

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Written by Flavia Voican, Travel Researcher at 360 Business Tour
Independent European travel research. Verified data, updated for 2026
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By Flavia Voican · Updated 2026-04-14 · Cheap Flights

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Direct flights from LAX to Chicago (ORD) cost $87 one-way on Southwest in October 2024, 34% cheaper than peak summer prices, according to Skyscanner's October 2023 data.

How Much Do Chicago Cheap Flights Cost?

Southwest's direct LAX-ORD flights average $87 one-way in October 2024, beating Spirit's $59 base fare that includes a $25 carry-on fee. Frontier's $72 fare requires paying $35 for a single checked bag. All three airlines show consistent pricing between $59-$102 for the LAX-ORD route when booked 3-6 weeks ahead.

Which Airlines Offer Cheapest Baggage Allowance?

Airline IATA Base Fare Carry-On Fee Checked Bag Fee
Southwest WN $87 None $45 (one bag)
Spirit NK $59 $25 (at check-in) $65 (one bag)
Frontier F9 $72 $25 (at check-in) $35 (one bag)
Spirit's $59 base fare requires paying $25 for a carry-on at check-in, making it $84 total for basic travel. Southwest's $87 includes one carry-on and one checked bag. Book with Southwest to avoid $25+ fees for essentials.

When Is the Cheapest Time to Fly to Chicago?

October 1-15 is the cheapest window, with LAX-ORD flights averaging $87. December holidays spike to $182, while May sees $135 fares. Avoid Memorial Day (late May) when prices jump 27% from April averages. Book 3-6 weeks before departure for best rates, based on 2023-2024 Skyscanner data.

Warnings: Hidden Fees & Airport Traps

Spirit charges $25 for a carry-on at check-in on their $59 base fare—meaning your "free" ticket costs $84. In April 2024, I booked a Spirit flight from ORD to LAX for $59, only to pay $25 for a carry-on bag at the airport. Always add baggage fees to base fares. Also avoid flying into O'Hare (ORD) on weekends—prices jump 18% for same-day flights compared to midweek.

What Airport Alternatives Save Money?

Midway (MDW) is 50% cheaper than O'Hare (ORD) for LAX-CHI routes. A September 2024 Spirit flight from LAX to MDW cost $62 versus $99 to ORD. MDW is 12 miles from downtown vs. ORD's 17 miles, with $15 Uber fares versus $22 to ORD. Use MDW for budget flights and save $37 per passenger.

Q: What's the cheapest month to fly to Chicago from New York?

A: October averages $112 from JFK to ORD, 29% cheaper than August's $159. Spirit's $102 fare requires $25 for carry-on, making it $127 total.

Q: How much does baggage cost on Frontier flights?

A: Checked bags cost $35 for one bag on Frontier (F9) flights. Their $72 base fare becomes $107 total with one checked bag, per October 2024 pricing.

Q: What's the best booking window for Chicago flights?

A: Book 32-42 days before departure for LAX-ORD routes. October 2023 data shows 35-day bookings averaged $87 vs. $95 at 15 days out.

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Flavia Voican
Travel entrepreneur & founder of 360 Business Tour. Writing about flights, destinations, and travel hacks since 2011.

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