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MSN to ORD

Madison to Chicago Flights

Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.

Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fare₹25,028Delta Air Lines
Fastest1h 13mgate to gate
Options found68flights on this route
Find your flight MSN ORD

Available Flights & Fares

Compare fares, timings and baggage. Pick the flight that suits your trip.

Prices in INR
68 flight options

Fares are checked again before payment.

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Delta Air Lines
Delta Air Lines
DL-5154
14:40
2026-11-14
Madison (MSN)United States flagDane County Regional
18H :24 M
1 Stop
MSP · 15h 21m Minneapolis (MSP), United States
09:04
2026-11-15
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Delta Air Lines
Delta Air Lines
DL-3982
19:49
2026-11-14
Madison (MSN)United States flagDane County Regional
13H :15 M
1 Stop
MSP · 10h 09m Minneapolis (MSP), United States
09:04
2026-11-15
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
United Airlines
United Airlines
UA-5902
05:00
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :20 M
Non Stop
06:20
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
AA
American Airlines
AA-4450
05:00
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :21 M
Non Stop
06:21
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-4440
06:02
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :28 M
Non Stop
07:30
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
United Airlines
United Airlines
UA-2137
06:25
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :19 M
Non Stop
07:44
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
United Airlines
United Airlines
UA-2037
08:15
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :16 M
Non Stop
09:31
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
AA
American Airlines
AA-4525
09:15
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :25 M
Non Stop
10:40
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
United Airlines
United Airlines
UA-5730
10:42
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :15 M
Non Stop
11:57
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 4 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
AA
American Airlines
AA-4717
11:16
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :23 M
Non Stop
12:39
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
United Airlines
United Airlines
UA-4455
12:43
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :19 M
Non Stop
14:02
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
United Airlines
United Airlines
UA-5781
15:00
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :19 M
Non Stop
16:19
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
AA
American Airlines
AA-4442
15:11
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :25 M
Non Stop
16:36
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
United Airlines
United Airlines
UA-5413
15:52
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :13 M
Non Stop
17:05
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
United Airlines
United Airlines
UA-5563
17:43
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :22 M
Non Stop
19:05
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
AA
American Airlines
AA-3346
19:09
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :21 M
Non Stop
20:30
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-4005
20:41
2026-11-14
Madison (MSN)United States flagDane County Regional
1H :14 M
Non Stop
21:55
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-1538
07:05
2026-11-14
Madison (MSN)United States flagDane County Regional
7H :07 M
1 Stop
DFW · 1h 59m Dallas (DFW), United States
14:12
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-1538
07:05
2026-11-14
Madison (MSN)United States flagDane County Regional
8H :55 M
1 Stop
DFW · 3h 49m Dallas (DFW), United States
16:00
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-2480
08:10
2026-11-14
Madison (MSN)United States flagDane County Regional
8H :00 M
1 Stop
CLT · 3h 29m Charlotte (CLT), United States
16:10
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-2139
11:37
2026-11-14
Madison (MSN)United States flagDane County Regional
6H :52 M
1 Stop
DFW · 1h 39m Dallas (DFW), United States
18:29
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-2139
11:37
2026-11-14
Madison (MSN)United States flagDane County Regional
8H :23 M
1 Stop
DFW · 3h 08m Dallas (DFW), United States
20:00
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces

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AA
American Airlines
AA-3026
12:23
2026-11-14
Madison (MSN)United States flagDane County Regional
5H :06 M
1 Stop
CLT · 0h 35m Charlotte (CLT), United States
17:29
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-1736
17:47
2026-11-14
Madison (MSN)United States flagDane County Regional
6H :12 M
1 Stop
DFW · 1h 00m Dallas (DFW), United States
23:59
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-3026
12:23
2026-11-14
Madison (MSN)United States flagDane County Regional
7H :48 M
1 Stop
CLT · 3h 08m Charlotte (CLT), United States
20:11
2026-11-14
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
AA
American Airlines
AA-6024
17:18
2026-11-14
Madison (MSN)United States flagDane County Regional
14H :09 M
1 Stop
PHL · 9h 19m Philadelphia (PHL), United States
07:27
2026-11-15
CHICAGO (ORD)United States flagO Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
No flights match the selected filters. Clear filters or open full search.

Airfare Highlights

From flights departing on Sat, 14 Nov 2026.

Lowest fare ₹25,028 Delta Air Lines 14:40
Earliest departure ₹29,437 United Airlines 05:00
Shortest duration ₹29,437 United Airlines 15:52
Night 00:00-05:59 ₹29,437 United Airlines at 05:00
Morning 06:00-11:59 ₹29,437 American Airlines at 06:02
Afternoon 12:00-17:59 ₹25,028 Delta Air Lines at 14:40
Evening 18:00-23:59 ₹25,028 Delta Air Lines at 19:49

Departure & Arrival Airport Details

Madison (MSN)

Dane County Regional

USA

Chicago (ORD)

O Hare International

USA

Flights shown for 14 Nov 2026. View all flights opens the complete search result.
Smart travel dates

Holidays and peak dates for Chicago

Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.

Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).

  • 11NovVeterans DayWednesday
  • 26NovThanksgiving DayThursday
  • 25DecChristmas DayFriday
  • 01JanNew Year's DayFriday
  • 18JanMartin Luther King, Jr. DayMonday
  • 12FebLincoln's BirthdayFriday

Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here, so check the exact date for your travel year.

Compare your journey

How to travel Madison to Chicago

Ways to make this trip that you can book on FlyX, compared by price and journey time.

OptionFromJourney timeAvailabilityAction
Non-stop flight Fastest₹29,4371h 13m15 flights
Connecting flight₹25,028Longer, includes a stop53 options

3 airlines operate this route.

Road distance and coach duration are approximate estimates from the air distance, not a timetable.

Airlines flying from Madison to Chicago

Compare fares, stops, baggage and refundability across the airlines flying this route.

American Airlines Flights

from ₹29,43725 flights
Fares from
₹29,437
Non-stop
7 in these results
Departures
25 in the list above

United Airlines Flights

from ₹29,43724 flights
Fares from
₹29,437
Non-stop
8 in these results
Departures
24 in the list above

Delta Air Lines Flights

from ₹25,02819 flights
Fares from
₹25,028
Non-stop
None in these results
Departures
19 in the list above

Route Overview & Flight Facts

Fastest flight duration1h 13m · United Airlines
First departure of the day05:00 · United Airlines
Last departure of the day20:41 · American Airlines
Flight options found68
Direct / non-stop options15
Airport codesMadison–MSN, Chicago–ORD

Fares and timings are indicative. The exact price is confirmed with the airline when you search.

Flight Schedule, Timings & Airfare Insights

Daily Flight Schedule & Travel Duration

The search for Sat, 14 Nov found 68 flight options, 15 of them non-stop. The first flight leaves around 05:00 and the last around 20:41. The fastest flight takes about 1h 13m.

Morning vs Evening Departure Fares

Lowest fare by departure window: Afternoon from ₹25,028, Evening from ₹25,028, Night from ₹29,437, Morning from ₹29,437. These observations do not predict the cheapest departure window on other dates.

Cheapest Airfare & Best Time to Book

Search your travel dates to compare current fares. Prices change with airline seat availability.

One-Way vs Round-Trip Fare Comparison

Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.

Online Web Check-In & Boarding Pass

Check the operating airline’s opening time and check-in deadline for each sector. Seat charges and availability depend on your fare. Use the airline reference and the links on Web Check-in.

How to Book Cheap Flights on FlyX

  1. 1
    Enter your travel details

    Choose one-way or round-trip, pick your dates and travellers in the search form above.

  2. 2
    Compare search results

    Sort or filter the Madison–Chicago results by price, departure time, stops and airline.

  3. 3
    Open the fare choices

    Check baggage allowance and refundability for each fare type before continuing.

  4. 4
    Review the final price

    Review the refreshed supplier fare, coupon saving and selected payment-method fee before you pay.

  5. 5
    Pay securely

    UPI, cards, net banking and wallets supported; payment and ticket issuance have separate statuses. If issuance is pending, follow the booking status; the confirmed ticket is sent after issuance.

Destination & City Travel Guide

About Chicago

Chicago’s downtown Loop puts Millennium Park, the Art Institute and the Riverwalk within a manageable area. The lakefront creates a second axis for walking, while neighbourhoods farther out need transit time of their own. Passengers landing at O’Hare may be changing flights or visiting relatives in the wider region, so check whether an overnight hotel is near the airport or downtown. The CTA Blue Line runs from the airport into the city and avoids the road congestion that can affect a taxi.

Read more about Chicago

Tips for travellers from India

The Loop is useful for the Art Institute, Millennium Park and central rail links, while a hotel near O’Hare serves an early flight or suburban appointment. These bases are a substantial distance apart. The CTA Blue Line reaches the airport from downtown, but passengers arriving at Terminal 5 first need the airport connection to the main rail-access area. The airport train and an intercity rail departure from Union Station are separate arrangements.

Air India uses Terminal 5. United domestic flights and international departures use Terminal 1, while many international arrivals are processed through Terminal 5, so an onward connection can involve a building change. In the city, pair the Art Institute with Millennium Park rather than crossing to a distant neighbourhood between them. The Riverwalk offers another central route, while the lakefront extends far beyond the downtown section. The Obama Presidential Center opened to the public in June 2026 in Jackson Park, creating a museum outing on the South Side rather than another stop beside the Loop. Plan that visit as its own district trip. A river architecture cruise also has a specific departure dock, which should be matched to the walking route. Choose between a museum-heavy day and a longer lakefront walk before booking several timed attractions.

Best time to visit Chicago

May to June or September to October, about 12–25°C, for river and lake walks.

Places to visit in Chicago

Millennium ParkArt Institute of ChicagoChicago RiverwalkNavy PierMuseum CampusDevon Avenue

How to reach Chicago

By Air: O’Hare International Airport (ORD) is about 27 km northwest of downtown Chicago; the CTA Blue Line takes about 45 minutes to the Loop. Taxis and booked cars also operate.

By Rail: Chicago Union Station serves intercity trains; the CTA Blue Line links O’Hare with downtown.

By Road: Airport taxis and app-based cars use expressways; intercity coaches use downtown stops.

What to do in Chicago

Walk from Millennium Park to the Art Institute.
Follow the Chicago Riverwalk.
Take an architecture cruise on the Chicago River.
Explore the lakefront around Museum Campus.

Chicago airport information

O’Hare International Airport (ORD). Air India operates from O’Hare Terminal 5. United uses Terminal 1 for domestic flights and international departures, while international arrivals without preclearance generally use Terminal 5.

Why Book Your Flight with FlyX?

Compare the available Madison to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.

Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.

Fare checked before paymentCoupon eligibility checkedBooking status trackingBooking support

Exclusive Flight Offers & Promo Coupons

Coupon codeOfferMax saving
FLYX20Up to 20% Off on Flights₹1,500

Check coupon eligibility and the final discount on the review page before you pay. View full terms.

Frequently Asked Questions

Is it worth booking Madison to Chicago flights in advance?

There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. On the Madison to Chicago dates shown on this page, the lowest fare is on a Saturday at ₹25,028. This can change from week to week.

How far is Madison from Chicago by air?

The flying distance depends on the routing the airline selects. The flight cards above show duration and stop details for each result.

Is there a direct flight from Madison to Chicago?

Yes. 15 non-stop flights are listed on this page for Madison to Chicago, operated by American Airlines and United Airlines. Use the Stops filter to see only those.

Which airlines fly Madison to Chicago?

American Airlines, United Airlines and Delta Air Lines are listed on this route for the dates shown here. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.

How long is the flight from Madison to Chicago?

The quickest non-stop Madison to Chicago flight on this page takes about 1h 13m. Non-stop flights here take between 1h 13m and 1h 28m. Journeys with a stop take longer, since the total includes the layover.

What is the cheapest Madison to Chicago flight fare?

The lowest Madison to Chicago fare on this page is ₹25,028. Fares on the same dates run up to ₹76,587, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.

Which is the cheapest airline for Madison to Chicago flight?

On this page, Delta Air Lines has the lowest Madison to Chicago fare, starting from ₹25,028. American Airlines is next, from ₹29,437. The cheapest airline can change with the date, so compare a few days around your trip.

What time do Madison to Chicago flights depart?

On the dates shown here, the first departure is around 05:00 and the last around 20:41, local time at Madison. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.

Why does the price change after clicking Book Now?

Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay. If it has moved, you see the new figure before any payment.

Before you book this route

Check the airport codes MSN–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.

Where these fares come from

The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price. Run a search to see what is available for your own dates.

Fares shown are for departures on .

Check official travel requirements

Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.

For payment, ticket issuance or a change request, see FlyX support. About FlyX.

What to Expect When Booking Your Flight

The MSN to ORD cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.

Before you book

Compare nearby dates

The date strip opens the complete search result for the route and selected date.

Use filters

Shortlist by price, stops, departure time and refundable fare preference.

Check fare choices

Continue to Booking opens the verified fare choices, including baggage and refundability, before review.

Lowest Madison to Chicago airfare, in 30 days and in 90 days

Cheapest FareFareDateAirlineDeparture
Lowest Airfare ₹25,028 14/11/2026 Delta Air Lines 14:40
Cheapest Airfare Within 30 Days ₹24,527 27/11/2026 Delta Air Lines 14:40
Cheapest Airfare Within 90 Days ₹23,777 26/01/2027 Delta Air Lines 14:40

Book Madison to Chicago Flight Tickets on FlyX

FlyX lists each Madison to Chicago flight in these results with its fare, departure time, stops, layover airport and baggage, so you can compare air tickets side by side. To find a cheap ticket, sort by price and check what baggage the fare includes. The fare is checked with the airline again before you pay.

Madison to Chicago flight duration is approximately 1 hour 13 minutes non-stop. There are 15 non-stop Madison to Chicago direct flights on the departure date shown on this page.

Madison to Chicago Flight Schedule and Timing

The search for these dates returned 68 flight options, 15 of them non-stop. The first departure from Madison is at 05:00 and the last is at 20:41. Flights leave from Dane County Regional and land at O Hare International.

Flight Route Details & Analysis

Flight DetailsInformation
RouteMadison to Chicago
Flight Duration1h 13m - 18h 39m
Airport CodesMadison - MSN, Chicago - ORD
Total Flights Available68 flights15 direct53 with layovers
First Flight DepartureDeparts at 05:00
Last Flight DepartureDeparts at 20:41
Early Morning Flights (12 AM - 8 AM)26 flights4 direct22 with layovers
Morning Flights (8 AM - 12 PM)17 flights4 direct13 with layovers
Afternoon Flights (12 PM - 4 PM)14 flights4 direct10 with layovers
Evening Flights (4 PM - 8 PM)10 flights2 direct8 with layovers
Night Flights (8 PM - 12 AM)1 flight1 direct0 with layovers

Airport Information & Terminals

MSN: Madison airport. Madison airport transfer should be matched to the exact hotel, suburb or meeting area. Rail can work well for light luggage, but late arrivals, winter weather and family baggage often make a direct cab or booked transfer easier.

ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
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