Cheap Flights to Chicago

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Cheap flights United States to Chicago
Flights from Chicago    Flights to Chicago

The HolidayPrice.com search engine will compare prices online and help you find the cheapest plane tickets to Chicago. We will compare flight offers on airline websites, at online travel agencies and at the booking offices of the airport in Chicago. All you need to do is choose the most suitable option of a ticket to United States.

Cheapest plane tickets to Chicago

Below you will find tickets for flights to Chicago, found by the users of HolidayPrice.com. The closer the departure date, the higher the cost; the most expensive tickets are for flights departing today and tomorrow.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
Flights
from $33 06 May 2025
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
Flights
from $47 07 May 2025
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
Flights
from $35 06 May 2025
Miami - Chicago WN 1626 Southwest Airlines Boeing 737
13:35 Fort Lauderdale Executive Airport
in a way 3 hours 0 min Direct
16:35 Chicago Midway
Flights
from $35 06 May 2025
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
Flights
from $81 07 May 2025
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from $39 05 May 2025
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44
in a way 2 hours 16 min Direct
05:00
Flights
from $39 05 May 2025
Washington - Chicago WN 1982 Southwest Airlines Boeing 737-700
15:00 Ronald Reagan National Airport
in a way 1 hours 50 min Direct
16:50 Chicago Midway
Flights
from $63 05 May 2025
Seattle - Chicago AA 1540 American Airlines Boeing 737-800
17:00 Seattle-Tacoma
in a way 3 hours 43 min Direct
20:43 O'Hare
Flights
from $49 07 May 2025
Atlanta - Chicago DL 1693 Delta Air Lines Boeing (Douglas) MD-88
17:25 Hartsfield-Jackson Atlanta
in a way 1 hours 35 min Direct
19:00 O'Hare
Flights
from $126 06 May 2025
Orlando - Chicago G4 2279 Allegiant Air Airbus A319
00:47 Orlando Sanford
in a way 2 hours 13 min Direct
03:00 Chicago Rockford
Flights
from $55 07 May 2025
Minneapolis - Chicago DL 667 Delta Air Lines Boeing 737-800
14:50 Saint Paul Island Airport
in a way 1 hours 10 min Direct
16:00 O'Hare
Flights
from $59 05 May 2025
Las Vegas - Chicago NK 456 Spirit Airlines Airbus A320
12:34 McCarran
in a way 2 hours 29 min Direct
15:03 O'Hare
Flights
from $44 06 May 2025
Charlotte - Chicago WN 536 Southwest Airlines Boeing 737-700
13:00 Charlotte Douglas
in a way 1 hours 45 min Direct
14:45 Chicago Midway
Flights
from $54 06 May 2025
Denver - Chicago WN 350 Southwest Airlines Boeing 737-700
05:35 Denver
in a way 2 hours 10 min Direct
07:45 Chicago Midway
Flights
from $30 05 May 2025
Philadelphia - Chicago AA 2098 American Airlines Boeing 737-800
14:00 Philadelphia
in a way 2 hours 0 min Direct
16:00 O'Hare
Flights
from $21 06 May 2025
Detroit - Chicago UA 5958 United Airlines Embraer 175
15:00 Detroit Metropolitan Wayne County Airport
in a way 1 hours 0 min Direct
16:00 O'Hare
Flights
from $32 07 May 2025
Tampa - Chicago WN 869 Southwest Airlines Boeing 737-800
13:50 Tampa
in a way 2 hours 30 min Direct
16:20 Chicago Midway
Flights
from $35 06 May 2025
Houston - Chicago WN 1065 Southwest Airlines Boeing 737-800
13:30 William P. Hobby Airport
in a way 2 hours 20 min Direct
15:50 Chicago Midway
Flights
from $39 07 May 2025
Beijing - Chicago HU 497 Hainan Airlines Boeing 787-900
08:40 Beijing Capital
in a way 12 hours 40 min Direct
21:20 O'Hare
Flights
from $652 07 May 2025
Amsterdam - Chicago KL 611 KLM Boeing 747-400
13:25 Schiphol airport
in a way 8 hours 30 min Direct
21:55 O'Hare
Flights
from $452 05 May 2025
Phuket - Chicago 9C 8758 Spring Airlines Airbus A320
08:20 Phuket
in a way 19 hours 50 min 1 Stopover
04:10 O'Hare
Flights
from $1 375 11 May 2025
Berlin - Chicago LH 175 Lufthansa Airbus A321
06:45 Tegel Airport
in a way 12 hours 15 min 1 Stopover
19:00 O'Hare
Flights
from $437 07 May 2025
Frankfurt - Chicago LH 430 Lufthansa Boeing 747-8i
11:45 Frankfurt Airport
in a way 9 hours 10 min Direct
20:55 O'Hare
Flights
from $449 05 May 2025
Denpasar - Chicago GA 880 Garuda Indonesia Boeing 777
16:45 Ngurah Rai
in a way 20 hours 45 min 1 Stopover
13:30 O'Hare
Flights
from $1 289 11 May 2025
Havana - Chicago WN 3953 Southwest Airlines Boeing 737-800
22:40 Jose Marti
in a way 6 hours 14 min 1 Stopover
04:54 O'Hare
Flights
from $313 11 May 2025
Tenerife - Chicago TP 1127 TAP Portugal Airbus A320 NEO
12:40 Tenerife South Airport
in a way 16 hours 42 min 2 Stopovers
05:22 O'Hare
Flights
from $516 11 May 2025
London - Chicago AA 99 American Airlines Boeing 787-800
09:45 Heathrow
in a way 8 hours 20 min Direct
18:05 O'Hare
Flights
from $347 06 May 2025
Seoul - Chicago KE 37 Korean Air Boeing 777-300ER
04:40 Incheon
in a way 12 hours 40 min Direct
17:20 O'Hare
Flights
from $591 07 May 2025
Athens - Chicago AA 161 American Airlines Boeing 787-800
14:15 Eleftherios Venizelos
in a way 11 hours 40 min Direct
01:55 O'Hare
Flights
from $719 05 May 2025
Colombo - Chicago UL 197 Srilankan Airlines Airbus A320
14:15 Bandaranaike
in a way 22 hours 15 min 1 Stopover
12:30 O'Hare
Flights
from $811 11 May 2025
Vienna - Chicago OS 65 Austrian Airlines Boeing 777-200
11:45 Vienna
in a way 10 hours 10 min Direct
21:55 O'Hare
Flights
from $386 05 May 2025
Lisbon - Chicago TP 229 TAP Portugal Airbus A330-200
14:00 Lisbon Portela Airport
in a way 9 hours 0 min Direct
23:00 O'Hare
Flights
from $439 11 May 2025
Thessaloniki - Chicago A3 500 Aegean Airlines Airbus A320
06:15 Thessaloniki
in a way 14 hours 0 min 1 Stopover
20:15 O'Hare
Flights
from $543 06 May 2025
Munich - Chicago UA 953 United Airlines Boeing 777
12:30 Franz Josef Strauss Airport
in a way 9 hours 35 min Direct
22:05 O'Hare
Flights
from $577 07 May 2025
Belgrade - Chicago LH 1411 Lufthansa Airbus A320 NEO
06:00 Belgrad Nikola Tesla Airport
in a way 13 hours 0 min 1 Stopover
19:00 O'Hare
Flights
from $384 07 May 2025
Delhi - Chicago AI 127 Air India Boeing 777-300ER
23:50 Indira Gandhi
in a way 15 hours 35 min Direct
15:25 O'Hare
Flights
from $541 07 May 2025
Riga - Chicago BT 101 airBaltic DeHavilland Dash 8 Q400
06:00 Riga
in a way 12 hours 35 min 1 Stopover
18:35 O'Hare
Flights
from $521 11 May 2025
Madrid - Chicago IB 6275 Iberia Airbus A340-600
12:35 Adolfo Suarez Madrid-Barajas Airport
in a way 9 hours 25 min Direct
22:00 O'Hare
Flights
from $461 06 May 2025
Varna - Chicago FB 972 Bulgaria Air Embraer 190
06:40 Varna Airport
in a way 18 hours 50 min 2 Stopovers
01:30 O'Hare
Flights
from $691 11 May 2025

The price of a ticket for a flight to Chicago depends on the class of the flight: economy, comfort or business class; on the presence of baggage or hand luggage; whether it is a one-way or a round-trip flight, a direct flight to Chicago or one with a transfer. The HolidayPrice.com search engine takes into account all of these factors, and always offers the best travel option.

Plane tickets from Chicago

Below you will find a selection of popular tickets for flights from Chicago airports and their prices. To purchase a ticket for a flight departing from Chicago, click on the “Buy” button opposite the destination you are interested in, and we will compare the cost.

Chicago - New York AA 2382 American Airlines Boeing 737-800
01:13 O'Hare
in a way 1 hours 47 min Direct
03:00 Newark Liberty
Flights
from $32 07 May 2025
Chicago - Los Angeles AA 2744 American Airlines Airbus A321
20:03 O'Hare
in a way 3 hours 57 min Direct
00:00 Los Angeles
Flights
from $46 05 May 2025
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from $35 05 May 2025
Chicago - San Francisco AA 1312 American Airlines Boeing 737-800
17:55 O'Hare
in a way 4 hours 5 min Direct
22:00 Norman Y. Mineta San Jose
Flights
from $61 07 May 2025
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $40 06 May 2025
Chicago - Washington WN 1450 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 1 hours 35 min Direct
15:15 Baltimore/Wash International Thurgood Marshall Airport
Flights
from $74 06 May 2025
Chicago - Seattle AA 1058 American Airlines Boeing 737-800
15:00 O'Hare
in a way 4 hours 0 min Direct
19:00 Seattle-Tacoma
Flights
from $41 05 May 2025
Chicago - Atlanta DL 2120 Delta Air Lines Boeing 717-200
18:36 Chicago Midway
in a way 1 hours 24 min Direct
20:00 Hartsfield-Jackson Atlanta
Flights
from $27 05 May 2025
Chicago - Orlando G4 2180 Allegiant Air Airbus A319
22:53 Chicago Rockford
in a way 2 hours 7 min Direct
01:00 Orlando Sanford
Flights
from $59 06 May 2025
Chicago - Minneapolis UA 1660 United Airlines Airbus A319
18:00 O'Hare
in a way 1 hours 0 min Direct
19:00 Saint Paul Island Airport
Flights
from $106 05 May 2025
Chicago - Las Vegas G4 226 Allegiant Air Airbus A319
20:41 Chicago Rockford
in a way 3 hours 27 min Direct
00:08 McCarran
Flights
from $43 05 May 2025
Chicago - Charlotte WN 489 Southwest Airlines Boeing 737-800
05:15 Chicago Midway
in a way 1 hours 40 min Direct
06:55 Charlotte Douglas
Flights
from $26 06 May 2025
Chicago - Denver AA 2885 American Airlines Boeing 737-800
19:50 O'Hare
in a way 2 hours 10 min Direct
22:00 Denver
Flights
from $35 05 May 2025
Chicago - Philadelphia AA 1948 American Airlines Boeing 737-800
16:19 O'Hare
in a way 1 hours 41 min Direct
18:00 Philadelphia
Flights
from $23 07 May 2025
Chicago - Detroit DL 3516 Delta Air Lines Canadair reg jet 700
21:08 Chicago Midway
in a way 0 hours 52 min Direct
22:00 Detroit Metropolitan Wayne County Airport
Flights
from $191 07 May 2025
Chicago - Tampa AA 2409 American Airlines Boeing 737-800
03:48 O'Hare
in a way 2 hours 12 min Direct
06:00 Tampa
Flights
from $47 05 May 2025
Chicago - Houston UA 1113 United Airlines Boeing 737-900
03:40 O'Hare
in a way 2 hours 20 min Direct
06:00 Marriot Astrodome
Flights
from $40 06 May 2025
Chicago - Beijing UA 851 United Airlines Boeing 777
20:55 O'Hare
in a way 13 hours 30 min Direct
10:25 Beijing Capital
Flights
from $745 06 May 2025
Chicago - Amsterdam KL 612 KLM Boeing 747-400
01:30 O'Hare
in a way 7 hours 40 min Direct
09:10 Schiphol airport
Flights
from $278 05 May 2025
Chicago - Phuket UA 835 United Airlines Boeing 777
16:00 O'Hare
in a way 23 hours 0 min 1 Stopover
15:00 Phuket
Flights
from $560 11 May 2025
Chicago - Berlin AA 150 American Airlines Boeing 787-800
01:15 O'Hare
in a way 11 hours 15 min 1 Stopover
12:30 Tegel Airport
Flights
from $327 05 May 2025
Chicago - Frankfurt LH 431 Lufthansa Boeing 747-8i
01:15 O'Hare
in a way 8 hours 10 min Direct
09:25 Frankfurt Airport
Flights
from $357 07 May 2025
Chicago - Denpasar WN 1264 Southwest Airlines Boeing 737-700
13:00 Chicago Midway
in a way 21 hours 40 min 2 Stopovers
10:40 Ngurah Rai
Flights
from $687 07 May 2025
Chicago - Havana UA 2335 United Airlines Boeing 737-800
15:32 O'Hare
in a way 5 hours 58 min 1 Stopover
21:30 Jose Marti
Flights
from $232 07 May 2025
Chicago - Tenerife TP 242 TAP Portugal Airbus A330-200
00:20 O'Hare
in a way 14 hours 10 min 2 Stopovers
14:30 Tenerife North Airport
Flights
from $505 11 May 2025
Chicago - London AA 90 American Airlines Boeing 787-800
18:15 O'Hare
in a way 7 hours 25 min Direct
01:40 Heathrow
Flights
from $233 07 May 2025
Chicago - Seoul KE 38 Korean Air Boeing 777-300ER
20:30 O'Hare
in a way 14 hours 0 min Direct
10:30 Incheon
Flights
from $419 06 May 2025
Chicago - Athens AA 160 American Airlines Boeing 787-800
01:25 O'Hare
in a way 10 hours 20 min Direct
11:45 Eleftherios Venizelos
Flights
from $468 06 May 2025
Chicago - Colombo UA 938 United Airlines Boeing 767-300
03:05 O'Hare
in a way 20 hours 0 min 1 Stopover
23:05 Bandaranaike
Flights
from $651 11 May 2025
Chicago - Vienna OS 66 Austrian Airlines Boeing 777-200
01:20 O'Hare
in a way 9 hours 0 min Direct
10:20 Vienna
Flights
from $484 05 May 2025
Chicago - Lisbon TP 228 TAP Portugal Airbus A330-200
01:00 O'Hare
in a way 7 hours 45 min Direct
08:45 Lisbon Portela Airport
Flights
from $342 07 May 2025
Chicago - Thessaloniki UA 907 United Airlines Boeing 767-300
23:55 O'Hare
in a way 12 hours 55 min 1 Stopover
12:50 Thessaloniki
Flights
from $488 05 May 2025
Chicago - Munich LH 437 Lufthansa Airbus A350-900
23:45 O'Hare
in a way 8 hours 35 min Direct
08:20 Franz Josef Strauss Airport
Flights
from $365 06 May 2025
Chicago - Belgrade UA 952 United Airlines Boeing 777
00:05 O'Hare
in a way 11 hours 30 min 1 Stopover
11:35 Belgrad Nikola Tesla Airport
Flights
from $344 07 May 2025
Chicago - Delhi AI 126 Air India Boeing 777-300ER
22:30 O'Hare
in a way 14 hours 15 min Direct
12:45 Indira Gandhi
Flights
from $488 07 May 2025
Chicago - Riga SK 946 Scandinavian Airlines Airbus A330-300
22:00 O'Hare
in a way 11 hours 10 min 1 Stopover
09:10 Riga
Flights
from $592 14 May 2025
Chicago - Madrid IB 6274 Iberia Airbus A340-600
00:40 O'Hare
in a way 8 hours 5 min Direct
08:45 Adolfo Suarez Madrid-Barajas Airport
Flights
from $348 05 May 2025
Chicago - Varna UA 958 United Airlines Boeing 767-300
21:55 O'Hare
in a way 15 hours 40 min 2 Stopovers
13:35 Varna Airport
Flights
from $577 11 May 2025
Chicago - Vilnius UA 907 United Airlines Boeing 767-300
23:55 O'Hare
in a way 12 hours 20 min 1 Stopover
12:15 Vilnius
Flights
from $342 05 May 2025
Chicago - Brussels UA 972 United Airlines Boeing 767-300
01:50 O'Hare
in a way 8 hours 0 min Direct
09:50 Brussels Airport
Flights
from $362 07 May 2025
To Chicago from $541! Airfare Deals by Air Serbia
from $541 left 127 days
Sales dates 01 May 2025 Flight dates: 07 June 2025
Berlin - Chicago One way, Economy - from $541
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Yerevan - Chicago One way, Economy - from $636
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Frankfurt - Chicago One way, Economy - from $654
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To Chicago from $1 136! Airfare Deals by Turkish Airlines
from $1 136 left 157 days
Sales dates 01 May 2025 Flight dates: 22 May 2025
Kazan - Chicago One way, Economy - from $1 136
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Yekaterinburg - Chicago One way, Economy - from $1 245
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To Chicago from $610! Airfare Deals by Qatar Airways
from $610 left 3 days
Sales dates 01 May 2025 Flight dates: 08 May 2025
Almaty - Chicago One way, Economy - from $610
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To Chicago from $794! Airfare Deals by Emirates
from $794 left 157 days
Sales dates 01 May 2025 Flight dates: 03 June 2025
Bishkek - Chicago One way, Economy - from $794
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To Chicago from $70! Airfare Deals by Spirit Airlines
from $70 left 10 days
Sales dates 01 May 2025 Flight dates: 14 May 2025
Baltimore - Chicago One way, Economy - from $70
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To Chicago from $139! Airfare Deals by Southwest Airlines
from $139 left 10 days
Sales dates 01 May 2025 Flight dates: 14 May 2025
Washington - Chicago One way, Economy - from $139
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Airports in 238 cities offer direct flights to Chicago

Popular cities from which you can fly direct to Chicago and back are: Phoenix, Dallas, Seattle, New York, Cincinnati. The cheapest flight to Chicago found in the last 48 hours by our customers at HolidayPrice.com is just from $ 24, on the route Fort Myers - Chicago. Planes fly to Chicago from 238 cities.

Phoenix from $ 29Dallas from $ 29Seattle from $ 70New York from $ 31Cincinnati
Cancun from $ 78Los Angeles from $ 54Las Vegas from $ 36Orlando from $ 45Miami from $ 30
San Francisco from $ 66Tampa from $ 25Boston from $ 47Minneapolis from $ 52Austin from $ 71
You can fly to Chicago from 35 countries

You can purchase tickets for direct flights to Chicago departing from 35 countries. The most popular countries of departure are: United States, Mexico, Canada, Costa Rica, India. The cheapest flight to Chicago on the route United States - Chicago (Fort Myers - Chicago), and costs from $ 24

United States from $ 24Mexico from $ 78Canada from $ 157Costa Rica from $ 205India from $ 481
United Arab Emirates from $ 354Puerto Rico from $ 64China from $ 618Poland from $ 235Belize from $ 295
Iceland from $ 389France from $ 225Sweden from $ 340Brazil from $ 331Finland from $ 333
53 airlines fly to Chicago

You can reach Chicago with the help of one of 53 airlines. The best air carriers that can help you get to this destination are: United Airlines, American Airlines, Southwest Airlines, Aer Lingus, Spirit Airlines. The fastest flight to Chicago is operated by United Airlines (UA 3767) on the route Milwaukee - Chicago. The airline's Canadair regional jet travels the distance between General Mitchell and O'Hare in an average of 00:30 minutes.

  • United Airlines
  • American Airlines
  • Southwest Airlines
  • Aer Lingus
  • Spirit Airlines
  • Frontier Airlines
  • Volaris
  • Delta Air Lines
  • Allegiant Air
  • Alaska Airlines
  • JetBlue Airways
  • Hainan Airlines
  • Air Canada
  • LOT Polish Airlines
  • Ethiopian Airlines
    • Types of airplanes that fly to Chicago

    There are 34 models of aircraft that fly to Chicago. The flights are operated by 53 airlines.

  • Boeing 737-800
  • Canadair regional jet
  • Boeing 737-700
  • Embraer RJ145
  • Canadair reg jet 700
  • Embraer 175
  • Boeing 777-300ER
  • Airbus A319
  • Airbus A320
  • Boeing 787-800
  • Embraer EMB 175
  • Boeing 777
  • Boeing 787-900
  • Boeing 737-900
  • Embraer ERJ-135/140/145 Regional Jet

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