Cheapest Newark to Chicago Flights: Insider Guide to Maximum Savings
Flying from Newark (EWR) to Chicago (ORD/MDW) doesn’t have to drain your travel budget. This bustling East Coast-to-Midwest corridor attracts millions of travelers annually, creating fierce airline competition that savvy travelers can leverage for incredible deals. Whether you’re heading to the Windy City for business, leisure, or a weekend escape, understanding the nuances of this route will transform your booking experience and put more money back in your pocket.
The Newark to Chicago flight market is one of North America’s most dynamic travel corridors. Multiple airlines compete aggressively, including United Airlines (with a major hub at Newark), Southwest, American, Delta, and budget carriers like Spirit and Frontier. This competitive landscape means prices fluctuate dramatically based on timing, demand patterns, and external factors. By mastering the strategies outlined in this guide, you’ll discover how to consistently find fares significantly below average rates.
Best Times to Book Your Flight
Timing your booking is crucial for snagging the lowest fares on Newark to Chicago routes. Industry research consistently shows that Tuesday and Wednesday departures offer the cheapest airfares, as these are traditionally slower travel days. Airlines price aggressively to fill seats mid-week, creating opportunities for budget-conscious travelers. Conversely, Friday through Sunday flights command premium prices as leisure travelers book weekend getaways.
The optimal booking window typically falls 1-3 months before your intended departure date. For this specific route, booking 6-8 weeks in advance often yields better results than last-minute bookings, contrary to popular belief. However, if you spot a sale, don’t hesitate—airline pricing algorithms can change within hours. Early morning flights (5:00 AM-7:00 AM departures) consistently cost 15-30% less than midday or evening options, though they require early wake-ups.
Avoid booking during peak travel seasons: spring break (mid-March to early April), summer vacation (June-August), Thanksgiving week, and the Christmas-New Year period. During these windows, even budget airlines maintain higher base fares. Instead, target the shoulder seasons in September-October and January-February when demand drops but weather remains reasonable.
Comparing Airlines on This Route
United Airlines dominates the Newark hub, offering frequent direct flights to both Chicago O’Hare (ORD) and Midway (MDW) airports. Their frequent service creates price competition, but they’re rarely the cheapest option. Southwest Airlines provides excellent value with free checked bags, no change fees, and competitive pricing. For ultra-budget travel, Spirit and Frontier offer rock-bottom base fares, though ancillary fees for baggage, seat selection, and carry-ons can offset savings.
American Airlines and Delta offer mid-range pricing with better service reliability than budget carriers. When comparing total costs, factor in baggage fees, seat selection charges, and other hidden expenses. A Spirit flight at $89 might cost $150 after fees, while a United flight at $129 might include checked luggage for frequent flyer members. Create a detailed cost comparison spreadsheet when evaluating options—the cheapest base fare isn’t always the best value.
Consider loyalty programs if you fly regularly. United MileagePlus members flying from Newark enjoy elite benefits and occasional discounted fares. Southwest Rapid Rewards and American AAdvantage programs offer similar perks. Even one free flight annually through accumulated points justifies signing up for airline newsletters and loyalty programs.
Money-Saving Strategies That Work
Understanding why flights are expensive helps you identify when prices drop. Set up price alerts on Google Flights, Hopper, and Kayak for your specific route. These tools notify you immediately when fares drop, allowing rapid booking before prices spike again. Configure alerts for your preferred travel dates and check them daily—many deals last only hours.
Flexible travel dates are your secret weapon. If your schedule permits, flying Tuesday instead of Friday can save $100-200 each way. Use Google Flights’ calendar view to visualize price patterns across an entire month. You’ll often notice dramatic price swings that correlate with specific days or dates. Being flexible with your travel window exponentially increases savings potential.
Clearing your browser cookies before searching for flights prevents airlines from tracking your search history and adjusting prices upward. Use incognito mode when researching fares, or try different browsers. Some travelers use VPN services to check fares from different locations, as airlines sometimes offer region-specific pricing. While not illegal, airlines actively combat this practice.
Consider the complete how to travel on a budget approach rather than fixating solely on flight costs. Sometimes booking a slightly more expensive flight that arrives at a better time or connects through a hub with cheaper ground transportation provides superior overall value. Factor in parking, rideshare costs, and hotel nights when evaluating options.
Alternative Airport Options
Newark Airport (EWR) sits just 15 miles from Manhattan, making it convenient for New York area residents. However, consider flying from LaGuardia (LGA) or JFK, which sometimes offer cheaper fares on the same route. Check all three New York area airports when searching—price differences can exceed $50 each way. Ground transportation costs might offset savings, so calculate total trip expenses, not just airfare.
On the Chicago end, Midway Airport (MDW) frequently undercuts O’Hare (ORD) pricing. Southwest Airlines particularly favors Midway, offering numerous daily flights at competitive rates. Midway sits just 10 miles southwest of downtown Chicago, actually closer than O’Hare for many travelers. Ground transportation from Midway is often cheaper and faster than from O’Hare, potentially offsetting any flight fare differences.
The Newark-to-Midway combination often yields the cheapest total journey costs. While this routing might seem less convenient than EWR-to-ORD, the savings justify exploring it. Research ground transportation options thoroughly—Chicago’s excellent public transit system (CTA) offers affordable rides downtown from both airports.
Best Booking Platforms
Google Flights remains the gold standard for flight searching, offering unmatched transparency, price tracking, and calendar views. Kayak and Skyscanner provide similar functionality with slightly different interfaces. These meta-search engines compare prices across hundreds of booking sites simultaneously, ensuring you see the lowest available fares.
Book directly with airlines when you’ve identified your preferred flight, as this eliminates third-party booking fees and provides better customer service if issues arise. Many airlines offer their lowest fares through direct booking. However, use meta-search engines to identify the cheapest option, then verify pricing on the airline’s website before committing.
Hopper specializes in price prediction, analyzing historical data to recommend optimal booking times. While not always accurate, Hopper’s insights prove valuable for understanding whether current prices represent good deals. The app’s “Buy Now” or “Wait” recommendations, though imperfect, guide decision-making effectively.
Advanced Travel Hacks
Hidden city ticketing involves booking a flight with a connection in your intended destination, then exiting at the connection point. For example, booking Newark-Chicago-Denver and exiting in Chicago. This works occasionally but violates airline terms of service and risks bag complications. Most travel experts don’t recommend this risky strategy despite rare savings.
Booking separate one-way tickets sometimes beats round-trip fares, especially when prices fluctuate significantly. Compare round-trip pricing against two separate one-way tickets before finalizing your booking. This strategy works best when booking weeks apart, allowing you to capture different price points.
Sign up for airline newsletters and follow airlines on social media. Southwest and Spirit frequently announce flash sales with 24-48 hour booking windows. These limited-time deals can offer incredible savings for flexible travelers. Set phone notifications for these airline social media accounts to catch sales immediately.
Consider traveling with carry-on luggage only when using budget carriers. Baggage fees ($30-50 per bag each way with Spirit/Frontier) dramatically increase total costs. Packing efficiently into a carry-on significantly reduces expenses and eliminates baggage claim waits.
Seasonal Price Patterns
January and February typically offer the cheapest fares as post-holiday travel demand plummets and winter weather discourages leisure travel. September and October present excellent opportunities as summer vacation ends and holiday travel hasn’t begun. These shoulder seasons combine relatively cheap flights with pleasant weather—ideal for budget-conscious travelers.
Late December through early January represents the most expensive period, with holiday travelers willing to pay premium prices. Summer (June-August) maintains consistently high prices due to family vacation demand. Spring break weeks see dramatic price spikes, with some flights doubling in cost compared to adjacent weeks.
Thanksgiving week is notoriously expensive, with flights reaching peak prices Wednesday through Sunday. If traveling for Thanksgiving, book early (4-6 months in advance) or travel before Wednesday or after Sunday for significant savings. Similarly, Christmas week represents the year’s most expensive travel period—avoid if possible.
Weather patterns influence pricing subtly. Severe winter weather sometimes causes price drops as travelers cancel, though this creates uncertainty. Conversely, perfect spring weather increases demand and prices. Understanding these patterns helps identify naturally cheaper travel windows.
Understanding ground transportation options in Chicago maximizes your savings. The CTA (Chicago Transit Authority) offers affordable transit from both airports. The Blue Line runs 24/7 from O’Hare to downtown, costing just $5. Midway’s Orange Line similarly connects downtown for $3. These options beat $40-60 rideshare costs significantly, especially for solo travelers or those not in hurries.
Hotel selection dramatically impacts overall trip costs. Budget chains like Motel 6, Red Roof Inn, and Super 8 cluster around airports and downtown, offering rates from $60-100 nightly. Airbnb sometimes beats hotels, particularly for longer stays or group travel. However, factor in cleaning fees and service charges when comparing prices. Research neighborhoods thoroughly—staying slightly farther from downtown but in safe, well-connected areas saves money without sacrificing accessibility.
FAQ
What’s the cheapest day to fly Newark to Chicago?
Tuesday and Wednesday departures consistently offer the lowest fares, typically 15-30% cheaper than weekend flights. Early morning departures (5:00-7:00 AM) add additional savings of 10-20% compared to midday or evening flights.
How far in advance should I book?
Book 6-8 weeks before your intended departure for optimal pricing on this route. However, if you spot a sale, book immediately—prices can change within hours. Set up price alerts to catch unexpected deals.
Is flying into Midway cheaper than O’Hare?
Yes, Midway typically offers cheaper fares, especially on Southwest Airlines. Additionally, ground transportation from Midway often costs less than from O’Hare, making it superior for budget travelers despite being slightly less convenient for some downtown locations.
What hidden fees should I expect with budget airlines?
Spirit and Frontier charge $30-50 per checked bag each way, $15-25 for carry-ons (if not the smallest size), and $5-10 for seat selection. These fees can double your base fare, so calculate total costs carefully before booking budget carriers.
Should I book round-trip or separate one-way tickets?
Compare both options before booking. One-way tickets sometimes beat round-trip pricing, especially when booking at different times. Use price comparison tools to evaluate both strategies for your specific dates.
What’s the best time of year to fly cheaply?
January-February and September-October offer the cheapest fares combined with reasonable weather. Avoid December-early January, summer (June-August), spring break, and Thanksgiving weeks when prices peak.
How can I ensure the cheapest booking?
Use incognito mode, check multiple airports (Newark, LaGuardia, JFK; O’Hare, Midway), set price alerts, remain flexible with dates, and book directly with airlines after identifying the cheapest option via meta-search engines.
The Newark to Chicago flight market rewards informed, flexible travelers willing to invest time researching options and remaining adaptable with travel dates. By implementing these strategies—booking during optimal windows, remaining flexible with dates and airports, comparing total costs rather than just base fares, and leveraging price alerts—you’ll consistently find flights well below average rates. Success requires patience and planning, but the savings justify the effort. Start tracking prices today, set up alerts, and prepare to book when opportunities arise. Your wallet will thank you when you land in the Windy City having paid a fraction of typical fares.
