Best Ways to Fly From LAX to Chicago (ORD) With Points
The best ways to fly from Los Angeles International Airport (LAX) to Chicago include redeeming Delta SkyMiles for an award ticket, using Frontier Miles for a low-cost flight to Chicago O’Hare International Airport (ORD), or booking Southwest Airlines with Rapid Rewards points for a trip to Chicago Midway International Airport (MDW). The most suitable option depends on award availability, travel dates, baggage needs, and whether reaching O’Hare or Midway is more convenient.
Travelers planning this route have several ways to use airline miles and points instead of paying the full cash fare. However, award prices can fluctuate, and the cheapest redemption is not always the best overall deal once taxes, baggage, seat selection, and airport transportation are considered.
This guide compares the main options, explains how each loyalty program works, and outlines practical strategies for finding better value on flights from Los Angeles to Chicago.
Related: Best Flights From Los Angeles (LAX) to Seattle (SEA): Guide
Los Angeles to Chicago: Route Overview
Los Angeles and Chicago are major U.S. travel markets, with flights connecting Southern California to the Chicago metropolitan area. Travelers generally need to compare two destination airports: Chicago O’Hare (ORD) and Chicago Midway (MDW).
| Route detail | What travelers should know |
| Departure airport | Los Angeles International Airport (LAX) |
| Primary destination airport | Chicago O’Hare International Airport (ORD) |
| Alternative destination airport | Chicago Midway International Airport (MDW) |
| Main airline options covered | Delta Air Lines, Frontier Airlines, Southwest Airlines |
| Loyalty programs | Delta SkyMiles, Frontier Miles, Southwest Rapid Rewards |
| Typical flight duration | Approximately four hours for a nonstop flight, depending on the route and conditions |
| Key booking consideration | Compare the complete trip cost, not just the points required |
Flight schedules, nonstop availability, and journey times vary by season and operating day. Travelers should check their preferred dates before deciding which airline or airport offers the best option.
O’Hare vs. Midway: Which Airport Is Better?
O’Hare is Chicago’s larger international airport and may be the more convenient arrival point for travelers staying in parts of the north, northwest, or far western suburbs. Midway is located southwest of downtown and can be convenient for visitors heading to central or southern parts of the city.
Neither airport is automatically better for every trip. The right choice depends on the final destination, ground transportation, arrival time, and the cost of the flight.
Southwest is an option for travelers considering Midway, while Frontier and Delta may be worth comparing for O’Hare itineraries. Travelers should confirm the airports served by their chosen flight before transferring points or booking a ticket.
1. Use Delta SkyMiles for Flights to Chicago
Delta SkyMiles is worth checking for travelers who have accumulated miles through Delta flights, eligible credit card spending, or participating rewards programs. The program can provide a way to book eligible flights between Los Angeles and Chicago without paying the entire base fare in cash.
Delta uses dynamic award pricing on many routes. That means the mileage requirement can change based on factors such as demand, travel dates, itinerary, and the specific flight selected. There is no single mileage price that guarantees a good redemption on every LAX-to-Chicago trip.
How to Search for Delta Award Flights
Travelers can check award availability through Delta’s official website.
- Enter Los Angeles (LAX) as the departure airport.
- Select Chicago O’Hare (ORD) or check alternative itineraries that serve Midway when available.
- Enter the preferred dates and passenger details.
- Select the option to search for flights using miles.
- Compare the mileage requirement, taxes, departure time, and any connections.
- Review the complete itinerary before confirming the reservation.
A flexible-date search can help identify days when the mileage cost is lower. If a nonstop itinerary is expensive in miles, a connecting flight may sometimes offer a better redemption, although the extra travel time should be considered.
When Delta SkyMiles Makes Sense
Delta SkyMiles may be a good fit for travelers who already have a useful balance of miles and find an award itinerary that compares favorably with the cash fare. It can also be useful for people who prioritize their preferred departure time or airline experience over finding the absolute lowest price.
Before redeeming, travelers should compare the cash ticket price with the miles required and the taxes due. A high mileage price for a relatively inexpensive cash ticket may provide less value than saving those miles for another trip.
2. Book Frontier Airlines Flights With Frontier Miles
Frontier Airlines is another option for the Los Angeles-to-Chicago route. Its low-cost model can appeal to travelers who want to minimize the base fare and are comfortable paying separately for optional services.
Frontier Miles can be redeemed for eligible Frontier-operated and marketed flights. Frontier publishes award flights starting at 5,000 miles one way, plus applicable taxes and fees, but this is a starting price rather than a guarantee for every route or date. Award seats and mileage requirements vary, and availability must be checked directly with the airline.
How Frontier Miles Redemptions Work
To search for a flight using Frontier Miles, travelers should sign in to their account and select the miles option when searching for flights. The booking results show the mileage requirement for available itineraries.
The final cost can include taxes, fees, and any applicable redemption charge. Frontier’s terms also specify that award tickets are subject to availability and that not every published route will necessarily have award seats available.
A low mileage requirement can make an award attractive, but the fare conditions matter. Basic tickets may not include advance seat assignments, carry-on baggage, checked baggage, or other optional services unless the applicable fare or bundle states otherwise.
Consider Frontier’s Bundles
Travelers who need additional services should compare the total price of the base fare with the available bundles. Depending on the option offered, a bundle may include benefits such as seat selection, baggage allowances, or added flexibility.
When comparing an award booking with a cash ticket, include any costs for:
- Carry-on and checked baggage
- Advance seat selection
- Preferred seating or other available extras
- Changes or cancellations, where applicable
- Taxes and award-related fees
These costs can significantly affect the value of a low-cost itinerary.
Is Frontier Miles a Good Deal?
Frontier Miles may suit travelers who are flexible about travel times, pack light, and find a low-mileage award on their chosen date. It can be especially attractive when the total cost of the award ticket and required extras remains lower than comparable alternatives.
Frontier also offers different award levels and bundled options, so travelers should review the actual itinerary rather than assume every award costs the minimum published number of miles. The airline’s official redemption information explains how to search and book with miles.
3. Use Southwest Rapid Rewards for Chicago Midway
Southwest Airlines provides another option for travelers flying from Los Angeles to the Chicago area, particularly those who are comfortable arriving at Chicago Midway International Airport (MDW).
Southwest Rapid Rewards points can be redeemed for eligible Southwest flights. Award prices are tied to the cash fare and the specific flight, so the number of points required can change as the ticket price changes. A higher cash fare will generally require more points than a lower-priced fare.
Because award pricing is dynamic, a fixed points figure should not be treated as a permanent price for LAX-to-MDW travel.
How to Book With Rapid Rewards Points
Travelers can search for award flights on Southwest’s website.
- Enter LAX as the departure airport and MDW as the destination.
- Add the travel dates and number of passengers.
- Choose the option to display prices in points.
- Compare the available flights and their point requirements.
- Review the itinerary, fare conditions, and applicable taxes.
- Confirm the booking only after checking the final details.
Travelers should compare multiple dates when possible. A departure one or two days earlier or later may offer a lower points price, depending on demand and the fares available.
How to Evaluate a Southwest Redemption
The best way to evaluate a Rapid Rewards redemption is to compare the cash fare with the points required for the same flight. The value can be estimated by subtracting the taxes and fees payable on the award ticket from the comparable cash price, then dividing the remaining amount by the points required.
For example, if a comparable cash fare costs $250 and the award requires 18,000 points plus $5.60 in taxes, the estimated value is:
($250 − $5.60) ÷ 18,000 = approximately 1.36 cents per point.
This is an illustrative calculation, not a live quote or a promise of a particular redemption value. Actual fares, award prices, and taxes vary by itinerary and date.
Remember the Airport Difference
Southwest’s Chicago service is relevant to travelers willing to use Midway rather than O’Hare. The airport choice should be based on the whole journey, not simply the points price.
A flight that costs fewer points may be less convenient if it arrives farther from the traveler’s hotel or requires more expensive ground transportation. Travelers should compare airport transfers, arrival times, and local transit options before booking.
Comparing the Main Points and Miles Options
The best program depends on the balance a traveler already holds, the flight schedule, and the cost of optional extras.
| Program | Airline | Chicago airport to consider | Main advantage | Important limitation |
| Delta SkyMiles | Delta Air Lines | Check ORD and available alternatives | Can offer useful award options for existing members | Mileage prices vary dynamically |
| Frontier Miles | Frontier Airlines | ORD, subject to current schedules | Low published starting award levels | Baggage, seats, and other extras can add costs |
| Southwest Rapid Rewards | Southwest Airlines | MDW | Points pricing tracks the cash fare | Award cost varies with fares and availability |
The table is a starting point for comparison, not a ranking that applies to every travel date. The lowest advertised award price may not be available for the desired itinerary, and flight schedules can change.
How to Find Better Value on LAX-to-Chicago Flights
Choosing a loyalty program is only one part of finding a good redemption. A few practical steps can help travelers compare options more effectively.
1. Compare Points With the Cash Fare
Do not assume that a ticket requiring fewer miles is automatically the better deal. Compare the cash price of the same or a similar itinerary against the points required, including the taxes and fees payable on an award ticket.
A cash fare may be more attractive when the price is low, especially if using points would consume a large portion of a loyalty balance.
2. Search Flexible Dates
If the travel dates are not fixed, compare several departure and return dates. Award prices and cash fares can vary considerably between weekdays, weekends, holidays, and busy travel periods.
Even modest flexibility can reveal a more convenient flight or a lower redemption price.
3. Compare Both Chicago Airports
Check O’Hare and Midway when both are practical for the trip. The final choice should account for the traveler’s destination in Chicago, transportation costs, and arrival time.
The savings from a cheaper flight can disappear if the ground journey is significantly more expensive or time-consuming.
4. Include Baggage and Seat Costs
Low-cost fares and award tickets may not include every service a traveler expects. Review the specific fare rules and determine whether a carry-on, checked bag, or advance seat selection is necessary.
Compare the total cost of the trip rather than relying on the base fare or mileage figure alone.
5. Check Award Availability Before Moving Points
Where a rewards program allows points transfers from eligible partners, travelers should verify that the desired flight is available and confirm the transfer terms before moving points. Transfers may not be reversible, and transfer times can vary.
Do not transfer points based only on a general estimate or an award price seen for a different date.
6. Consider the Value of a Connection
A connecting itinerary may sometimes require fewer miles or cost less in cash than a nonstop flight. However, travelers should consider the extra time, connection length, and potential disruption if the first flight is delayed.
A small saving may not justify a long layover, particularly for a short domestic trip.
7. Recheck the Final Price Before Booking
Airline schedules, fares, award inventory, and program rules can change. Confirm the current mileage requirement, taxes, baggage terms, and cancellation conditions directly with the airline before completing the reservation.
Final Thoughts
The best way to fly from Los Angeles to Chicago with points depends on the traveler’s preferred airport, loyalty balances, schedule, and budget. Delta SkyMiles can be worth checking for suitable award itineraries, Frontier Miles may appeal to travelers seeking a low-cost flight, and Southwest Rapid Rewards is an option for those heading to Chicago Midway.
The most effective strategy is to compare award prices with cash fares, account for baggage and transportation, and verify current availability directly with each airline. By evaluating the full trip cost instead of focusing only on the points required, travelers can make a more informed choice for their LAX-to-Chicago journey.
Frequently Asked Questions
There is no single cheapest option for every date. Travelers should compare Delta SkyMiles, Frontier Miles, and Southwest Rapid Rewards for the desired dates and calculate the total cost after taxes, baggage, seat selection, and transportation. The lowest available redemption depends on current pricing and award inventory.
Frontier advertises award flights starting at 5,000 miles one way, plus applicable taxes and fees. That is a general starting level, not a guaranteed price for the LAX-to-Chicago route. Travelers should search their exact dates on Frontier’s website to see the current requirement.
Delta SkyMiles can be useful when an award itinerary offers a reasonable mileage price compared with the cash fare. Because award prices can vary, travelers should check several dates and compare the final cost before redeeming.
Yes. Travelers can use Rapid Rewards points for eligible Southwest flights, including itineraries to Chicago Midway when available. The number of points required varies with the fare and flight selected, so current award pricing should be checked before booking.
The best airport depends on where the traveler is staying and how they plan to reach their final destination. O’Hare and Midway serve different parts of the Chicago area, so transportation time and cost should be considered alongside the airfare.
No. Award tickets can provide good value, but the result depends on the points required, cash fare, taxes, fees, and any additional services. A low cash fare may be more economical than using a large number of points for the same trip.
Travelers should begin comparing options once their dates are reasonably clear and monitor prices if they have flexibility. There is no universal booking window that guarantees the lowest award price. Availability and pricing depend on the airline, route, season, and demand.