Cheap Denver to Chicago Flights: Insider Tips for Smart Travelers

Finding affordable Denver to Chicago flights requires strategy, timing, and insider knowledge that most casual travelers overlook. This route, connecting Colorado’s Mile High City with the Windy City, is one of America’s busiest domestic corridors—which means opportunities abound for savvy bookers willing to dig deeper. Whether you’re planning a business trip, visiting family, or embarking on a midwest adventure, understanding the nuances of this market can save you hundreds of dollars.

Denver International Airport (DEN) and Chicago’s O’Hare (ORD) and Midway (MDW) airports see constant competition among carriers like Southwest Airlines, United, American, and budget carriers. This competition creates pricing volatility that, when monitored properly, presents incredible deals. The 900-mile journey typically takes 2-2.5 hours of flight time, making it an ideal distance for both budget and premium carriers to operate efficiently. Let’s explore the proven tactics that turn expensive tickets into bargains.

Best Times to Book Denver to Chicago Flights

The golden rule for securing cheap Denver to Chicago flights is understanding booking windows. Research from major travel analytics firms consistently shows that the optimal booking period falls between 1-3 months before your departure date. For domestic routes like Denver-Chicago, this window is particularly powerful because airlines adjust pricing based on demand forecasting models.

Tuesday and Wednesday typically offer the lowest fares, as airlines release discounted inventory early in the week to fill seats. Many carriers price their tickets around 3 PM Eastern Time on Tuesdays, making this the sweet spot for price drops. Setting price alerts for these specific days can yield savings of $50-150 per ticket. Conversely, weekend bookings—Friday through Sunday—consistently show 15-25% higher prices as leisure travelers shop for getaways.

Early morning flights departing Denver between 5-7 AM and red-eyes leaving after 10 PM consistently offer 20-30% discounts compared to mid-morning and afternoon departures. These less desirable times exist because most travelers prefer convenient schedules, creating predictable pricing patterns. If your schedule permits flexibility, these windows represent genuine savings opportunities. Many business travelers unknowingly overpay by booking convenient times when cheaper options exist just hours earlier or later.

Price Tracking and Monitoring Tools

Modern technology eliminates guesswork from flight shopping. Price tracking software monitors Denver to Chicago flights continuously, alerting you when fares drop below your target price. Google Flights’ price tracking feature allows you to monitor specific routes and receive notifications, while Hopper uses artificial intelligence to predict whether prices will rise or fall in the coming days.

Kayak and Skyscanner offer similar functionality with customizable alerts. Set your maximum acceptable price—perhaps $120 one-way—and these tools notify you when fares meet your criteria. This passive monitoring approach eliminates the anxiety of wondering whether you’re getting a good deal. Many travelers report saving 30-40% simply by waiting for algorithmic alerts rather than booking immediately.

Browser extensions like Honey and Capital One Shopping integrate directly into airline websites, highlighting when better prices appear elsewhere. These tools compare prices across multiple booking platforms simultaneously, ensuring you never miss a cheaper option. Additionally, airline websites themselves often feature flash sales: Southwest’s “Ding” app and United’s app notifications announce surprise deals within hours of release.

Set up price alerts on our travel blog for comprehensive flight deal coverage alongside these automated tools. Combining human expertise with algorithmic monitoring creates the most effective strategy.

Budget Airlines and Hidden City Ticketing

Southwest Airlines dominates the Denver-Chicago market, offering frequent daily flights with no change fees and two free checked bags. Their Business Select fares cost more upfront but often provide better value when factoring in flexibility and included amenities. Frontier and Spirit occasionally offer ultra-cheap fares ($50-80 one-way), though their baggage policies and seat selection fees require careful cost analysis.

A controversial tactic called “hidden city ticketing” involves booking a flight with a connection beyond your actual destination, then exiting at your intended stop. For example, booking Denver-Chicago-Boston and departing in Chicago technically violates airline terms of service. While it occasionally yields savings, airlines increasingly penalize this practice through frequent flyer account closures and legal threats. The ethical and practical risks typically outweigh modest savings.

Instead, legitimately compare all carriers’ total costs including baggage, seat selection, and potential change fees. Southwest’s transparent pricing often beats competitors when you factor in these hidden costs. United Airlines and American Airlines offer competitive fares with status-matching programs for frequent flyers, while their extensive route networks provide flexibility.

Seasonal Pricing Patterns

Seasonal demand dramatically influences Denver to Chicago flight prices. Summer months (June-August) see peak pricing due to vacation travel, with average fares 40-60% higher than winter rates. Spring break (mid-March through early April) creates secondary price spikes as families travel. Holiday periods—Thanksgiving week, Christmas through New Year’s, and Easter—command premium pricing.

Winter months (January-February, excluding holidays) offer the absolute cheapest fares, with average one-way tickets dropping to $80-120. September and early October provide excellent value as summer vacation season ends and fall break travel hasn’t peaked. Late April through May represents another sweet spot with moderate demand and lower prices.

If you’re considering winter travel destinations, the Denver-Chicago route becomes even more economical during this season. Flexible travelers who can shift their plans toward off-season dates routinely save $200-400 on round-trip tickets.

Business travel patterns also influence pricing. Mid-week flights during business hours (Tuesday-Thursday, 9 AM-5 PM) cost more due to corporate travel demand. Avoiding these times when possible provides consistent savings.

Airport Selection Strategy

Denver serves only one major commercial airport (DEN), but Chicago offers two: O’Hare (ORD) and Midway (MDW). Midway typically features cheaper fares because it hosts Southwest Airlines’ major hub, creating competitive pricing. Flights to Midway often cost $20-50 less than equivalent O’Hare flights. However, consider ground transportation costs: Midway sits 20 miles south of downtown, while O’Hare sits 17 miles northwest. Public transit costs roughly $5 from either airport, but ride-share costs vary.

For Denver departures, DEN is your only option, but its extensive carrier competition keeps prices competitive. The airport’s modern facilities and efficient operations mean reasonable layover times if connecting through Denver to other destinations.

If you’re exploring top travel destinations for 2025, consider whether a Chicago stopover enhances your itinerary. Sometimes booking Denver-Chicago-another destination as a single ticket costs less than separate bookings.

Loyalty Programs and Credit Card Rewards

Frequent flyer programs transform Denver to Chicago flights from expenses into subsidized travel. United Airlines’ MileagePlus, American’s AAdvantage, and Southwest’s Rapid Rewards all offer robust earning potential on this route. Sign-up bonuses for travel credit cards—typically 50,000-75,000 bonus miles—can cover entire round-trip tickets immediately.

The Southwest Rapid Rewards Premier Business Credit Card offers 60,000 bonus points ($750 travel credit) after spending $5,000 within three months. For Denver-Chicago travelers, this essentially provides free flights for a year. American Express Platinum and Chase Sapphire Reserve cards offer 50,000-100,000 bonus points through various promotions, translating to $500-1,200 in travel value.

Beyond credit card bonuses, everyday spending earns miles. Paying for rental cars, hotels, and restaurants with airline-branded credit cards accumulates points toward free flights. Many business travelers completely eliminate flight costs through disciplined credit card strategy combined with business expense reimbursement.

Loyalty program members receive early access to sales, bonus mile promotions, and upgrade opportunities. Even without elite status, enrolling in free programs provides price alerts and special member fares unavailable to non-members.

Day of Week and Time Considerations

Beyond Tuesday/Wednesday booking patterns, departure day selection influences pricing significantly. Tuesdays, Wednesdays, and Saturdays consistently offer lower fares than Fridays and Sundays. This reflects business travel patterns: executives fly out Thursday-Friday and return Sunday-Monday, while leisure travelers prefer long weekends.

If you’re planning a trip that could extend to other destinations beyond Chicago, consider multi-city bookings. Flying Denver-Chicago-another city sometimes costs less than separate bookings, especially when airlines compete for connecting passengers.

Red-eye flights (departing 10 PM-6 AM) consistently cost 25-35% less than daytime flights. While sleeping on planes isn’t ideal, the savings justify the inconvenience for budget-conscious travelers. Arriving in Chicago early morning allows a full day of exploration after minimal sleep.

Early morning flights (5-7 AM departures) also offer discounts, though less dramatically than red-eyes. These flights appeal to business travelers, so savings are modest. However, arriving by late morning provides an entire afternoon and evening in Chicago.

Combining Strategies for Maximum Savings

The most aggressive savers combine multiple tactics simultaneously. Set price alerts for Tuesday/Wednesday bookings 6-8 weeks before departure, targeting early morning or late evening flights to Midway Airport. Ensure your airline credit card signup bonus aligns with your booking, and check for flash sales through airline apps.

For example: Book a Wednesday early morning flight to Midway 7 weeks before departure using miles earned from a travel credit card signup bonus. This approach frequently yields free or nearly-free flights. Add flexibility to your dates, and savings multiply exponentially.

Business travelers should negotiate corporate rates with airlines while simultaneously leveraging personal loyalty programs and credit card rewards. Many companies maintain preferred airline agreements offering 10-15% discounts, which stack with other promotions.

Consider whether alternative destinations might offer better value. Sometimes competing cities have cheaper flights, and a short rental car drive becomes more economical than premium airfare.

Round-trip bookings occasionally cost less than one-way tickets, especially on this competitive route. Even if you only need one direction, purchasing round-trip and abandoning the return leg sometimes saves money compared to one-way fares—though airline terms of service technically prohibit this practice.

Ground Transportation and Hidden Costs

Cheap flight prices mean nothing if ground transportation consumes savings. Denver International Airport offers RTD light rail service downtown for $10.50, but this takes 37 minutes. Ride-share (Uber/Lyft) typically costs $25-40 to downtown Denver. Parking at DEN ranges from $18-35 daily, making multi-day trips expensive.

Chicago’s situation mirrors this. Midway offers the Blue Line CTA train to downtown for $5, taking 25-40 minutes. O’Hare’s Blue Line costs $5 and takes 40 minutes. Ride-share from either airport costs $30-50 to downtown. Budget these costs when comparing Denver to Chicago flights against driving alternatives.

Many travelers overlook that cheap flights sometimes make driving competitive. A 900-mile drive from Denver to Chicago takes 13-14 hours. Gas costs roughly $120 (assuming $3.50/gallon and 25 MPG), while wear-and-tear adds another $80-100. Splitting driving over two days adds hotel costs. However, avoiding airport parking, security lines, and baggage fees might justify driving for some trips.

For budget-conscious travelers, combining cheap flights with free attractions in Chicago maximizes value. The Chicago Museum of Art, 606 Trail, and lakefront offer zero-cost entertainment. Affordable neighborhoods like Pilsen and Logan Square provide budget lodging and restaurants.

Advanced Booking Strategies

Sophisticated travelers monitor travel blogs and forums for Denver to Chicago flight deals shared by other enthusiasts. Websites like FlyerTalk and SlickDeals host communities dedicated to finding flight bargains. These communities share real-time alerts when prices drop unexpectedly or airlines announce sales.

Airline error fares—tickets priced incorrectly due to system glitches—occasionally appear. These $30-50 fares for normally $150+ flights exist briefly before airlines correct mistakes. Deal-sharing communities catch these errors and alert members within minutes. Following these communities requires daily monitoring but yields occasional spectacular savings.

Airline newsletters provide advance notice of sales before public announcements. Signing up for Southwest’s email list, United’s MileagePlus newsletter, and American’s AAdvantage updates alerts you to promotional fares 1-2 days before general availability. This head start allows booking before prices increase.

Incognito/private browsing prevents airlines from tracking your searches and artificially inflating prices based on repeat visits. While airlines claim this doesn’t happen, many travelers report lower prices when using private browsing. It’s a simple, zero-cost tactic worth implementing.

Booking through airline websites directly rather than third-party sites occasionally reveals exclusive fares unavailable elsewhere. Additionally, airline websites simplify rebooking if flight changes become necessary, avoiding third-party intermediary complications.