Whether you're planning a business trip or a city escape, finding flights to Chicago at a competitive fare starts with comparing travel dates, airports, and airline options. Chicago combines iconic architecture, world-class museums, waterfront attractions, and a celebrated food scene. This guide explains how to find affordable airfare, choose between O'Hare and Midway, compare airlines, and make informed booking decisions without overlooking baggage fees or other travel costs.
Why Book Flights to Chicago for Your Next Trip?
Chicago, Illinois, is a major US destination for business, leisure, cultural experiences, and international travel. Its extensive airline network connects the city with destinations across the United States and around the world.
Whether you're visiting for a weekend getaway, a family holiday, or a business meeting, Chicago offers attractions for different interests and budgets.
- Architecture: Discover Chicago's celebrated skyline on an architectural river cruise.
- Top attractions: Explore Millennium Park, the Art Institute of Chicago, Navy Pier, and the Willis Tower Skydeck.
- Food experiences: Try deep-dish pizza, Chicago-style hot dogs, and neighbourhood restaurants.
- Entertainment: Enjoy live blues, jazz venues, sporting events, and seasonal festivals.
- Business connections: Benefit from extensive domestic and international flight options.
With two major commercial airports, travellers can compare different routes and schedules to find an itinerary that suits their plans.
How to Find Cheap Flights to Chicago
Finding cheap flights to Chicago requires more than choosing the lowest advertised ticket price. Travel dates, baggage requirements, airport selection, and connection times all affect the overall cost of your journey.
Use these practical strategies to find better-value flights to Chicago.
1. Compare Flexible Travel Dates
Check fares across different dates and departure times. Shifting your trip by a day or two may help you find cheaper flights.
2. Book in Advance
Start checking fares weeks or months ahead, especially for international trips and peak seasons. Book when the price and travel conditions suit you.
3. Consider Off-Peak Travel
January, February, and some autumn dates may offer lower fares on certain routes. Prices vary by departure city, holidays, and demand, so check actual fares before booking.
4. Compare the Total Ticket Price
Check baggage, seat selection, and other fees before booking. Compare the total cost, not just the base fare, across full-service and budget airlines.
5. Consider Connecting Flights
A connecting flight may cost less than a nonstop option but adds travel time and the risk of missed connections.
6. Monitor Last-Minute Fares
For last minute airfare to Chicago, check both airports and different departure times. Prices fluctuate, so last-minute savings aren't guaranteed.
7. Compare Booking Options Through Wizfair Travels
Compare fares, baggage fees, and ticket conditions through Wizfair Travels to find flights that fit your budget and schedule.
Chicago Airports: O'Hare vs. Midway
Chicago has two major passenger airports: O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). When searching for cheap tickets, compare available fares and fly to Chicago affordably based on your travel dates, preferred airport, destination within the city, and overall budget.
| Feature | O'Hare International Airport (ORD) | Midway International Airport (MDW) |
| Location | Northwest of downtown Chicago | Southwest of downtown Chicago |
| Route selection | Extensive domestic and international connections | Many domestic routes and selected international services |
| Major airline presence | United Airlines, American Airlines, and other carriers | Southwest Airlines, Delta Air Lines, Frontier Airlines, and other carriers |
| Public transportation | CTA Blue Line (runs 24/7, reaches downtown Chicago in ~40 to 45 minutes) | CTA Orange Line (Direct "L" train service connects downtown Chicago's Loop in ~20 to 25 minutes) |
| Consider it if | You find a suitable international or domestic itinerary | Its schedule, fare, or location better suits your plans |
Note: Routes, schedules, travel times, and fares may change. Confirm current details with official sources before travelling.
Which Chicago Airport Should You Choose?
- Choose O'Hare if it offers a better flight schedule, a convenient international connection, or a lower overall fare.
- Consider Midway if its available routes and arrival times better match your plans.
Money-saving tip: Compare the complete journey cost, including airfare, baggage, airport transfers, and onward transportation. A cheaper ticket may not represent better value if getting to your final destination costs considerably more.
Which Airlines Offer Flights to Chicago?
Several major airlines operate services to Chicago. Comparing routes and flight deals to Chicago can help you find suitable fares and nonstop options based on your departure city and travel dates.
Top Airlines Flying to Chicago
- American Airlines: Flies to O'Hare (ORD) and accounts for about 31% of arrivals. Average one-way fares are around $390.
- United Airlines: Serves O'Hare (ORD) and accounts for about 31% of arrivals. Average one-way fares are around $380.
- Southwest Airlines: Flies to O'Hare (ORD) and Midway (MDW), accounting for about 12% of arrivals. Average one-way fares are around $220.
- Delta Air Lines: Serves both ORD and MDW, accounting for about 8% of arrivals. Average one-way fares are around $290.
- Frontier Airlines: Flies to ORD and MDW, accounting for about 4% of arrivals. Average one-way fares are around $160, making it a budget-friendly option.
Note: Airline arrival percentages and average one-way fares are approximate estimates and may change with routes, travel dates, demand, and availability. Check current fares before booking.
Top Routes to Chicago
Chicago connects travellers with major cities across the United States and destinations worldwide. When comparing flights to Chicago, review these one-way economy fares to explore options that fit your travel budget.
- New York (JFK/LGA): $52
- Los Angeles (LAX): $38
- Newark (EWR): $82
- Boston (BOS): $89
- Orlando (MCO): $66
- Atlanta (ATL): $33
- Fort Lauderdale (FLL): $69
- Dallas (DFW/DAL): $57
- Minneapolis (MSP): $59
- Nashville (BNA): $96
Note: Fares may vary by travel dates, availability, booking window, season, the selected airline, and destination airport (ORD or MDW).
Best Time to Book and Fly to Chicago
Chicago welcomes visitors throughout the year, but weather, holidays, festivals, and business events can affect airfare and accommodation prices.
| Season | What to Expect | Booking Advice |
| Winter | Cold weather, possible snow, and busy holiday periods | Compare January and February dates while allowing flexibility for weather disruptions |
| Spring | Changing temperatures and increasing outdoor activity | Check prices around school holidays and major events |
| Summer | Popular sightseeing season, festivals, and waterfront activities | Compare fares early if your dates are fixed |
| Autumn | Cooler weather, fall colours, and cultural events | Compare September and October fares across several dates |
There is no single cheapest month for every route. Your departure airport, travel dates, airline competition, and local events all influence ticket prices.
For a better chance of finding cheap air fare to Chicago, compare multiple travel dates, monitor fare changes, and review both airports where practical. Midweek departures may be cheaper on some routes, but always check actual prices rather than assuming a particular day offers the best deal.
How to Save Money Beyond Airfare
Your total Chicago travel budget includes more than the plane ticket. A few practical decisions can help you control additional expenses.
- Use public transport: CTA rail services connect both airports with downtown Chicago.
- Choose accommodation strategically: Compare the total hotel cost, location, and access to public transportation.
- Check baggage rules: Review your airline's luggage allowance to avoid unexpected charges.
- Plan attraction visits: Check official ticket prices, opening hours, and reservation requirements before visiting popular sights.
- Explore local restaurants: Neighbourhood eateries and casual dining spots can offer alternatives to expensive tourist-area restaurants.
- Use eligible rewards: Airline miles and credit card rewards may reduce travel costs, subject to their terms and availability.
Planning these expenses alongside your airfare gives you a clearer picture of your complete trip budget.
Important: When comparing flights and booking tickets to Chicago, look beyond the airfare. Consider baggage allowances, seat selection, connection duration, cancellation conditions, and the total journey time.
Top Attractions to Explore After Your Flight to Chicago
Once you arrive, Chicago offers plenty to explore, whether you are visiting for a few days or planning a longer stay.
- Millennium Park: See Cloud Gate, popularly known as The Bean, and enjoy the surrounding public spaces.
- Chicago Riverwalk: Walk beside the river and admire the city's distinctive architecture.
- Navy Pier: Discover waterfront attractions, restaurants, and seasonal entertainment.
- Art Institute of Chicago: Explore an internationally recognised art collection.
- Willis Tower Skydeck: Enjoy elevated views of Chicago's skyline.
- Magnificent Mile: Browse shops, restaurants, and well-known city landmarks.
Check current opening hours, ticket prices, and seasonal availability when planning your itinerary.
Ready to Find Better Flight Deals to Chicago?
Finding affordable flights to Chicago starts with comparing fares, airports, baggage fees, and ticket conditions. Explore available options through Wizfair Travels, compare itineraries, and choose a flight that suits your budget and schedule. Plan your Chicago trip with confidence.
FAQs
Which month is cheapest for flights to Chicago?
January, February, and some autumn dates may offer competitive fares on certain routes. The cheapest month depends on your departure city, travel dates, and demand. Compare a flexible calendar to identify suitable prices.
Which airport is better for Chicago, ORD or MDW?
O'Hare offers extensive domestic and international connections, while Midway serves many domestic routes and has convenient rail access to downtown. Compare fares, schedules, baggage costs, and onward transportation before deciding.
Which airlines offer nonstop flights to Chicago?
United Airlines, American Airlines, and other carriers operate nonstop flights on selected routes. Availability depends on your departure city, destination airport, and travel dates.
How far in advance should I book flights to Chicago?
Start comparing fares several weeks or months before departure. Booking ahead can provide more choice for peak-season and international trips, but no advance-booking period guarantees the lowest price.
Are connecting flights cheaper than nonstop flights?
Connecting flights can cost less on some routes, but not always. Compare the total fare, additional travel time, baggage charges, and connection risks before booking.
How can I find last-minute flights to Chicago?
Compare current fares across airlines, departure times, and both Chicago airports. Check baggage costs and connection conditions before purchasing. Last-minute fares can increase or decrease depending on demand and seat availability.
How do I get from Chicago airport to downtown?
The CTA Blue Line connects O'Hare with downtown Chicago, while the Orange Line connects Midway with downtown. Taxis, rideshares, and other ground transportation options are also available.
Is it possible to find cheap flights to Chicago?
Yes, affordable fares are available on some routes and dates, but prices vary. Compare flexible dates, different airlines, both airports, and the complete ticket cost to find an option that fits your budget.
