Cheap Flights Denver to Chicago: Insider Advice for Budget-Conscious Travelers
The Denver to Chicago route is one of America’s most popular domestic flights, connecting the Mile High City with the vibrant Windy City. Whether you’re planning a business trip, a weekend getaway, or a longer adventure, finding affordable airfare can significantly stretch your travel budget. This guide reveals insider secrets and practical strategies that savvy travelers use to score the best deals on flights from Denver to Chicago.
Flying between these two major hubs offers excellent opportunities for savings if you know when to book, which airlines to watch, and how to leverage the right tools. The distance of approximately 900 miles typically translates to flight times around two hours, making this a convenient corridor for both leisure and business travelers. Understanding the dynamics of this route can help you save hundreds of dollars on your next trip.
Best Times to Book Denver to Chicago Flights
Timing is everything when hunting for cheap flights. Industry research consistently shows that booking 21-30 days in advance typically yields the lowest fares on domestic routes like Denver to Chicago. However, this isn’t a hard rule—flexibility is your greatest asset. Mid-week flights, particularly Tuesday through Thursday departures, tend to be 15-25% cheaper than weekend flights because business travelers dominate weekend routes.
The sweet spot for booking often falls on Tuesday or Wednesday afternoons, when airlines adjust their pricing strategies in response to competitor moves. Avoid booking on Fridays, Sundays, and Mondays, as these days see increased demand and higher prices. Early morning departures (5:00 AM to 7:00 AM) and late evening flights (after 8:00 PM) consistently offer better rates than mid-day options, though you’ll sacrifice convenience for savings.
If you’re flexible with your travel dates, aim for shoulder seasons—spring (April-May) and fall (September-October)—rather than peak summer or winter holidays. These periods offer significantly lower fares while still providing pleasant weather in Chicago. Winter months (January-February) can be surprisingly affordable, though weather considerations may apply.
Airlines and Carriers on This Route
Multiple carriers compete on the Denver-Chicago corridor, which creates opportunities for price wars and special promotions. Southwest Airlines dominates this route with frequent daily flights, and their two free checked bags policy often makes them cheaper than competitors when factoring in baggage fees. United Airlines operates several flights daily and occasionally offers competitive pricing, especially for connecting flights through Chicago’s O’Hare hub.
Frontier Airlines, based in Denver, frequently offers rock-bottom fares on this route, though their ultra-low-cost model means you’ll pay extra for carry-ons, seat selection, and checked bags. For budget travelers willing to accept minimal amenities, Frontier can deliver incredible deals. Allegiant Air occasionally serves this route with promotional pricing but operates less frequently than other carriers.
Major carriers like American, Delta, and United sometimes offer competitive rates, particularly when they’re running promotions or facing capacity pressures. Don’t automatically dismiss legacy carriers—their fares can surprise you, especially if you’re booking far in advance or traveling during less popular times. Sign up for airline newsletters to receive exclusive flash sales and promotional offers.
Money-Saving Strategies That Work
Beyond basic booking timing, several proven strategies can unlock additional savings. Incognito browsing prevents airlines from using cookies to track your searches and potentially raising prices based on your interest. Clear your cookies or use your browser’s private mode every time you search for flights. Some travelers swear by searching from different locations or using VPNs, though this has become less effective as airlines have adapted.
Consider flying into or out of Chicago Midway Airport (MDW) instead of the more popular O’Hare (ORD). Midway often has cheaper fares and less congestion, plus it’s actually closer to downtown Chicago. Similarly, if you have flexibility, compare prices from Denver International (DEN) with nearby regional airports, though limited service makes alternatives less practical from Denver.
Booking one-way flights separately instead of round-trip tickets sometimes yields savings, particularly if airlines are competing aggressively on one leg of your journey. Use comparison sites to check both options before committing. If you’re traveling for work, check whether your employer offers corporate travel discounts through negotiated rates with airlines or travel management companies.
Join airline loyalty programs even if you’re not a frequent flyer. Credit card sign-up bonuses often provide enough miles for a free flight, and elite status can bring unexpected perks. Southwest’s Rapid Rewards and United’s MileagePlus programs are particularly valuable on this route given their frequency and market presence.
Price Tracking Tools and Alerts
Technology makes finding cheap flights easier than ever. Google Flights offers excellent price tracking with calendar views showing fares across entire months. Set up price alerts for your Denver to Chicago route, and Google will email you when prices drop below your target threshold. The calendar feature instantly reveals which days offer the cheapest options.
Kayak, Skyscanner, and Momondo are powerful meta-search engines that compare prices across hundreds of booking sites simultaneously. Kayak’s price forecast feature predicts whether fares will rise or fall in coming days, helping you decide whether to book immediately or wait. These tools often find deals that individual airline websites don’t display prominently.
Hopper is an app specifically designed for flight price predictions. It analyzes billions of flight prices and uses machine learning to advise whether you should book now or wait for better prices. The app sends notifications when prices drop significantly for your tracked routes. Secret Flying and Scott’s Cheap Flights email newsletters alert subscribers to exceptional deals, though most flights require flexibility or advance planning.
Set up alerts on multiple platforms rather than relying on a single tool. Different search engines sometimes access different inventory, and you might catch a great deal that others miss. Check alerts daily if you’re flexible on dates—the best deals disappear quickly once posted.
Alternative Airports and Flexibility
While Denver and Chicago are major hubs with excellent connectivity, exploring alternatives can sometimes reveal savings. Regional airports near Denver like Fort Collins-Loveland (FNL) or Colorado Springs (COS) occasionally offer competitive fares, though limited service makes them less practical. The drive time usually outweighs any savings unless you’re staying in those areas.
From Chicago’s perspective, Midway Airport (MDW) is genuinely competitive and often cheaper than O’Hare. Midway is also easier to navigate, closer to downtown, and less crowded. South Bend (SBN) and Indianapolis (IND) are further alternatives, but the drive time makes them impractical unless you’re combining your Chicago trip with visits to those regions.
If you’re flexible on your destination, consider whether nearby cities might work. Flights from Denver to Las Vegas sometimes cost less than Chicago flights, and you could connect through Las Vegas cheaply. Similarly, exploring Houston to NYC flights or Seattle to San Diego flights on different dates might reveal cheaper alternatives if you’re flexible about where you ultimately travel.
Flexibility with travel dates remains your most powerful tool. Being able to shift your trip by even a few days can save $100-300 per ticket. If your schedule permits, compare prices across a 7-10 day window to identify the absolute cheapest days.
Seasonal Pricing Patterns
Understanding seasonal trends on the Denver-Chicago route helps you anticipate price movements. Summer months (June-August) see peak prices as families travel and tourists visit Chicago’s attractions. Winter holidays (December 20-January 3) are expensive due to holiday travel demand. Spring break (mid-March through early April) creates price spikes as families book getaways.
The cheapest periods are typically January-February (post-holiday lull), early May (before summer begins), September (back-to-school period discourages leisure travel), and early November (before Thanksgiving rush). These shoulder seasons offer the best combination of low prices and pleasant weather for exploring Chicago.
Understanding why prices fluctuate helps you plan strategically. Business travel peaks Monday-Thursday, driving up weekday prices in normal times. Summer leisure travel reverses this pattern, with weekends becoming more expensive. Holiday periods see across-the-board increases regardless of day of week.
Check best winter travel destinations guides if you’re flexible on where to go—sometimes traveling during winter to less popular destinations saves money while still providing excellent experiences. Similarly, exploring underrated places to travel and discovering hidden gems around the world can reveal cheaper alternatives to major cities during peak seasons.
Hidden Fees and How to Avoid Them
Advertised prices don’t always reflect true costs. Budget airlines like Frontier charge $10-50 for carry-on bags, $35-50 for checked bags, $5-10 for seat selection, and $5-15 for printing boarding passes. A seemingly cheap $89 Frontier fare can easily become $180 once fees are added. Southwest’s inclusion of two free checked bags and free seat selection makes their higher base fares surprisingly competitive.
Baggage fees vary significantly by airline. United and American charge $30 for the first checked bag, $40 for the second. Southwest includes two free checked bags. If you’re checking luggage, factor these costs into your comparison. For Denver to Chicago trips, many travelers can pack carry-on only and avoid these fees entirely.
Seat selection fees range from free (Southwest) to $5-25 per seat (other carriers). Premium seat selections (exit rows, extra legroom) cost significantly more. If you don’t mind random seat assignments or middle seats, you can avoid these fees. Booking directly with airlines sometimes waives fees for elite members or credit card holders.
Credit card processing fees, change fees, and cancellation policies vary by airline and ticket type. Basic economy fares are often non-refundable with expensive change fees. Spending an extra $20-30 for a flexible ticket often makes financial sense if your plans might change. Always read the fine print before finalizing your purchase.
Travel insurance is optional but worth considering if your trip involves non-refundable hotels or activities. Trip insurance typically costs 5-10% of your ticket price but can save you hundreds if you need to cancel. Compare insurance options before assuming you need it—credit cards and airlines sometimes provide coverage automatically.