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Best Cheap Airfare Deals to Chicago in 2025 - Save Big on Your Next Trip!

Travel Tips | 02 Nov 2025

Best Cheap Airfare Deals to Chicago in 2025 - Save Big on Your Next Trip!

Chicago, the Windy City, is a must-visit for its architectural marvels, deep-dish pizza, and Lake Michigan beaches— all yours for a steal with the right cheap airfare deals to Chicago. Planning your 2025 getaway? You're in luck. As of October 25, 2025, roundtrip cheap flights to Chicago start as low as $48 from Dallas, with non-stops under $58 from Baltimore and $66 from Denver. Whether you're eyeing budget flights to ORD from New York, Los Angeles, or Atlanta, Cheap Deals Fare crushes competitors like Kayak and Expedia by offering exclusive Chicago flight deals up to 30% lower, powered by our 600+ airline network. From affordable roundtrip flights to Chicago to insider hacks on the best time to book flights to Chicago, we've got the scoop to maximize your savings. Let's deep-dive into these cheap airline tickets to Chicago and get you to the Loop without breaking the bank!

Why Chicago? The Ultimate Midwest Escape

Chicago blends urban energy with lakeside charm, drawing 55 million visitors yearly to its Millennium Park, Willis Tower Skydeck, and Navy Pier fireworks. As a major hub via O'Hare (ORD) and Midway (MDW), it's a breeze for domestic hops—expect 1-5 hour flights from most US cities. The magic? Cheap airfare deals to Chicago make it accessible, especially in shoulder seasons. November 2025 brings crisp 40-50°F temps for architecture boat tours and holiday markets, without summer crowds (June-August, 70-80°F). If you're searching cheap flights to Chicago from major cities, now's ideal—fares average $316 domestically, per Google Flights, but our deals drop it lower. No wonder it's a top spot for festivals like Lollapalooza or Taste of Chicago.

Sizzling 2025 Deals: Cheap Flights to Chicago from US Hubs

Prices dip in October-May, but our scans for November 2025-January 2026 reveal cheap flights to Chicago under $100 roundtrip from key gateways. These economy fares include taxes; opt for midweek Tuesdays for 10% savings. Cheap Deals Fare aggregates from Spirit, Frontier, United, Delta, and American—beating Kayak's $48 baseline with flash codes like CHIDeal25 ($25 off).

Top budget airfare deals to Chicago table (roundtrip economy):

Departure City

Airport

Sample Dates (2025)

Airline

Stops

Price (Roundtrip)

Duration (Outbound)

Dallas (DFW)

DFW

Nov 12 - Nov 19

Spirit

0

$48

2h 20m

Baltimore (BWI)

BWI

Nov 15 - Nov 22

Frontier

0

$58

2h 10m

Denver (DEN)

DEN

Nov 18 - Nov 25

United

0

$66

2h 40m

Los Angeles (LAX)

LAX

Dec 2 - Dec 9

American

0

$119

4h 10m

New York (JFK)

JFK

Nov 11 - Nov 18

Delta

1

$139

3h 50m

Atlanta (ATL)

ATL

Nov 19 - Nov 26

Southwest

0

$100

2h

Las Vegas (LAS)

LAS

Dec 3 - Dec 10

Spirit

0

$67

3h 50m

*Prices from Kayak, Expedia, and Cheap Deals Fare searches—grab 'em quick as cheap roundtrip flights to Chicago fluctuate! For example, Spirit's DFW non-stop hits $48, while United's DEN direct is $66. West Coasters from LAX save with directs under $120; East from JFK via one-stops. Pro tip: Cheap flights to ORD from USA average $241 if booked 64 days out.

Score the Best Cheap Airfare Deals to Chicago: Pro Hacks

Nailing cheap flights to Chicago? It's all strategy. Cheap Deals Fare tops Expedia's tools with alerts and bundles—here's how to slash costs on affordable flights to Chicago:

  • Book 1-3 Months Ahead: For December trips, act now—fares jump $200 within 21 days. Hopper data flags 40 days out for lows like $49.

  • Best Time to Book Flights to Chicago: October-May rules cheapest ($90k avg. intl., $200s domestic); avoid July peaks (4% hike). Shoulder seasons like September-October save 10%.

  • Cheapest Day to Fly to Chicago: Tuesdays ($98 avg.); Saturdays costliest ($110). Afternoon flights shave $10-20.

  • Aggregator Alerts: Set "US to CHI" on Cheap Deals Fare or Google Flights for drops like $25 one-ways from Vegas.

  • Opt for Budget Carriers & Stops: Frontier/Spirit lead $48 deals; one-stops from NYC save 25% vs. directs.

  • Miles & Packages: Redeem Delta SkyMiles; bundle via Cheap Deals Fare for $300 hotel + flight combos.

Flash: Use CHIDeal25 at Cheap Deals Fare for $25 off—better than Expedia's no-fee perks.

Optimal Timing for Cheap Flights to Chicago & Weather Scoop

For cheap airfare deals to Chicago, February-May or September-October shine—mild 50-70°F for Blues Fest or architecture tours, fares 10-20% below peaks. Skip January chills (18°F) or August rains. November 12, 2025, flags lowest fares per Skyscanner. Events like Magnificent Mile Lights add sparkle sans spikes.

Chicago forecast (October 25, 2025): Crisp 55°F—November mirrors for cozy deep-dish nights.

ORD & MDW Guide: Chicago Airport Essentials

Cheap flights to Chicago land at O'Hare (ORD, world's 3rd busiest, 88M passengers) or Midway (MDW, domestic focus). ORD: 16 miles from Loop—CTA Blue Line ($5, 45 mins), taxis ($40, 30-60 mins traffic), or GO Airport Express shuttles ($30). MDW: Closer (9 miles), Orange Line ($3, 25 mins). Rentals shuttle free; Global Entry ($100) zips customs. Cheap Deals Fare's status tool tracks delays.

Budget Adventures in Chicago: Stretch Your Savings

Your cheap airline tickets to Chicago booked—now thrive on $50/day:

  • Millennium Park & Cloud Gate: Free "Bean" selfies, summer concerts.

  • Art Institute of Chicago: $32 entry (free Thursdays), Impressionist gems.

  • Navy Pier: Gratis fireworks, $15 Centennial Wheel.

  • Willis Tower Skydeck: $30 panoramic views.

  • Deep-Dish at Lou Malnati's: $15 slices, walking tours free.

Extend to Wrigley Field ($20 tours) or Lakefront Trail hikes—2025's youth jobs program adds free events.

Lock in Your Cheap Airfare Deals to Chicago Now!

The Windy City's calling—cheap flights to Chicago at $48 are live! Secure your budget flights to ORD on Cheap Deals Fare with CHIDeal25 before hikes. From cheap roundtrip flights to Chicago to savvy best time to book flights to Chicago, what's your must-do? Comment below and wind your way affordably!

Disclaimer: Fares change rapidly; verify on Cheap Deals Fare. Updated October 25, 2025.

- By cheapdealsfare Team
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*Fares incl. all fuel surcharges, our service fees and taxes. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. Lowest fares may require an advance purchase of up to 21 days.
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