Cheap Flights from Chicago to Denver: Complete Insider Guide

Finding affordable flights from Chicago to Denver doesn’t require luck—it requires strategy. This popular Midwest-to-Mountain West corridor offers consistent opportunities for budget-conscious travelers willing to book smart. Whether you’re heading to Denver for outdoor adventures, business meetings, or mountain town exploration, we’ve compiled insider tips that consistently save travelers $100-300 on roundtrip fares.

The Chicago to Denver route is one of America’s most competitive flight paths, with multiple carriers battling for passengers daily. This competition creates excellent opportunities for savvy bookers. From timing your purchase to understanding airline pricing patterns, mastering these techniques transforms your travel budget and opens doors to more frequent mountain getaways.

Best Time to Book Flights Chicago to Denver

Timing your booking is perhaps the single most important factor in securing cheap flights. Research consistently shows that booking 1-3 months in advance yields the lowest fares on the Chicago-Denver route. For domestic flights like this corridor, the sweet spot typically falls 45-60 days before departure.

Tuesday and Wednesday departures are historically cheaper than Friday-Sunday flights. If your schedule permits flexibility, shifting your travel by just two days can save $75-150 per ticket. Airlines adjust pricing based on demand patterns, and midweek travel sees significantly lower passenger volume.

The time of day matters too. Early morning departures (6-8 AM) and late evening flights (9 PM+) consistently price lower than convenient afternoon slots. While less glamorous, these time slots reward flexible travelers with substantial savings. A 6:45 AM departure might cost $120 less than the same day’s 2 PM flight.

Check out our guide on how to travel on a budget for comprehensive strategies beyond just flights. We also cover similar booking patterns for Chicago to London flights, where international booking windows operate differently.

Budget Airlines & Carrier Comparison

The Chicago-Denver corridor features competition from major carriers and budget alternatives, each with distinct pricing strategies:

• Southwest Airlines: Offers two free checked bags and no change fees, making total trip cost competitive even if base fare seems higher. Their frequent sales and rapid rewards program provide excellent value for repeat travelers.
• Frontier Airlines: Denver’s home carrier offers rock-bottom base fares but charges for carry-ons and seat selection. Calculate total cost including fees before assuming it’s cheapest.
• United Airlines: Competitive pricing with frequent sales, especially for premium economy upgrades. Their hub status in Denver creates more schedule options.
• American Airlines: Often matches competitor pricing and offers status benefits for frequent flyers. Their Charlotte connection provides viable alternatives to direct flights.
• Delta Air Lines: Premium positioning but frequent sales and better service consistency justify higher base fares for some travelers.

Ultra-budget carriers charge separately for everything: seat selection ($15-35), carry-on bags ($35-50), checked luggage ($30-40), and beverages. A “$89” Frontier fare becomes $165+ after realistic add-ons. Compare apples-to-apples by calculating total trip cost, not just advertised base fares.

Seasonal Price Patterns & Sweet Spots

Denver’s altitude, outdoor attractions, and ski proximity create distinct seasonal pricing patterns. Understanding these patterns helps you identify genuine deals versus false bargains.

Winter (December-February): Ski season drives premium pricing, especially December holidays and Presidents’ Day weekend. However, January 7-31 (post-New Year, pre-Presidents’ Day) offers excellent deals as holiday travelers depart. This period sees some of the year’s cheapest fares.

Spring (March-May): Easter week commands high prices, but March and early April offer moderate fares. May represents peak spring travel with stable, moderate pricing. Mother’s Day weekend sees increases.

Summer (June-August): Peak season with consistently high fares. July is most expensive. However, early June (before schools release) and late August (post-peak) offer relative bargains within summer’s elevated pricing structure.

Fall (September-November): September offers excellent value as summer ends and holiday season hasn’t begun. October features stable, moderate pricing. Thanksgiving week is expensive; November’s first two weeks offer outstanding deals.

The absolute cheapest periods: January 7-31, early June, late August, and early-to-mid November. These windows combine low demand with reasonable weather and few major holidays.

Advanced Booking Strategies

Beyond basic timing, advanced techniques separate savvy travelers from average bookers:

Price Alerts & Monitoring: Set up Google Flights, Kayak, and Hopper alerts for your route. These services notify you of price drops, enabling reactive booking when fares dip. Track prices for 2-3 weeks before booking to understand your route’s pricing baseline.

Incognito Browsing: Airlines track repeat searches and may increase prices for users showing high interest. Use private/incognito browsing when comparing fares to avoid algorithmic price increases. Clear cookies between searches.

Flexible Date Search: Use calendar view in search engines to compare prices across entire months. Sometimes flying Tuesday instead of Wednesday saves $200. This visualization reveals patterns invisible in single-date searches.

One-Way vs. Roundtrip: Surprisingly, booking two one-way tickets sometimes beats roundtrip pricing, especially when combining different carriers. This flexibility requires more comparison but yields savings on volatile routes.

Hidden City Ticketing Warning: While technically possible, booking Chicago-Denver with a connection beyond Denver (then skipping the final leg) violates airline terms and risks account suspension. We don’t recommend this risky strategy.

Learn more about Denver to Chicago flights for return journey strategies, which often employ different pricing models than outbound legs.

Airport Hacks & Alternative Routes

Chicago offers two major airports; Denver has one. Understanding each airport’s role in your pricing strategy maximizes savings:

Chicago Airports: O’Hare (ORD) is the major hub with most flights and competitive pricing. Midway (MDW) sometimes offers cheaper fares, especially on Southwest. The 30-minute drive difference between airports is worth investigating for $100+ savings.

Denver International (DEN): Colorado’s only major airport, so limited alternatives exist. However, checking nearby Rocky Mountain region airports (Colorado Springs, Fort Collins) reveals no practical savings given drive times.

Connecting Flights: Direct flights Chicago-Denver typically cost more than connecting flights through hubs like Dallas, Charlotte, or Minneapolis. A connection adding 3-4 hours might save $80-150. Evaluate whether time savings justify the price premium for your schedule.

Multi-City Bookings: If you’re planning flights from Chicago to Orlando or other secondary destinations, booking Chicago-Denver-Orlando as a multi-city ticket sometimes costs less than separate bookings.

Package Deals: Flight+hotel bundles from Expedia, Costco Travel, and airline-specific packages often beat separate bookings. Even if hotel rates seem high, the flight discount frequently compensates.

Travel Tips for Denver Adventures

Once you’ve booked your cheap Chicago-Denver flight, maximize your mountain adventure:

Getting from DEN to Downtown: Skip expensive airport taxis. The RTD light rail ($10.50) connects directly to downtown Denver in 37 minutes. It’s reliable, frequent, and costs 85% less than rideshare.

Denver’s Best Budget Neighborhoods: Stay in RiNo (River North) or Five Points for authentic Denver culture at lower rates than downtown hotels. These neighborhoods feature excellent restaurants, breweries, and galleries without premium pricing.

Free Denver Attractions: Explore the South Platte River, Washington Park, and downtown’s public art installations without spending beyond transportation. The Denver Art Museum offers pay-what-you-wish hours Tuesday evenings.

Mountain Day Trips: Rocky Mountain National Park, Red Rocks, and Mount Evans are accessible from Denver. Plan these excursions during your stay to maximize your mountain experience from your affordable flight investment.

Brewery Tours: Denver’s craft beer scene offers free tastings and affordable brewery tours. The free walking tour of LoDo (Lower Downtown) covers history, architecture, and local culture.

Timing Return Flights: Book return flights for late evening or early morning to maximize Denver time. A 10 PM departure lets you enjoy a full day before heading to the airport.

FAQ

What’s the average price for flights Chicago to Denver?

Typical roundtrip fares range $180-320 for economy seats booked 6-8 weeks in advance. Off-peak periods (January, early November) see fares around $150-220. Peak summer and holiday weeks reach $300-450. Booking at optimal times saves $100+ versus last-minute purchases.

Which airline offers the cheapest flights Chicago to Denver?

Frontier consistently offers lowest base fares but charges for carry-ons and seat selection. Southwest provides competitive pricing with included bags and free changes. United and American match competitor pricing strategically. Compare total cost including all fees rather than base fares alone.

Is it cheaper to fly into a different Denver-area airport?

Denver International (DEN) is the only commercial airport serving the metro area. Colorado Springs (COS) is 90 minutes south—the drive cost and time typically exceed any fare savings. Stick with DEN.

How far in advance should I book Chicago to Denver flights?

Book 45-60 days before departure for optimal pricing. Avoid booking more than 4 months ahead (prices increase) or within 2 weeks (last-minute premium). Monitor prices 2-3 weeks before your ideal booking window to catch unexpected sales.

Are Tuesday flights really cheaper than Friday flights?

Consistently, yes. Tuesday-Thursday departures average 15-25% cheaper than Friday-Sunday flights on this route. This pattern holds across seasons. If your schedule permits midweek travel, substantial savings await.

Should I book roundtrip or two one-way tickets?

Roundtrip typically offers better value on stable routes. However, if return dates are flexible or you’re combining carriers, two one-way tickets may beat roundtrip pricing by $30-80. Use both search methods and compare.

What’s the best day of the week to book flights?

Tuesday through Thursday mornings historically show the lowest prices, as airlines match competitor pricing from Monday evening. Avoid booking Friday-Sunday when prices stabilize at higher levels. Tuesday 3-4 AM offers the theoretical sweet spot.

Can I save money with connecting flights?

Absolutely. Connecting flights save $80-150+ compared to direct flights, though they add 3-5 hours to travel time. Evaluate your time value—for leisure trips, connections often make financial sense.

Are there hidden fees I should know about?

Budget airlines charge for carry-ons ($35-50), seat selection ($15-35), and checked bags ($30-40). Southwest includes two free checked bags and free changes. Factor these fees into total cost comparisons. A “cheap” $89 Frontier fare becomes $165+ with realistic add-ons.

What if prices drop after I book?

Most airlines offer free cancellation or rebooking within 24 hours of purchase. Some allow free changes even after 24 hours if rebooking is cheaper. Check your airline’s specific policy. Set price alerts to catch significant drops and rebook if you’re within the policy window.