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Cheap flights from Chicago

Cheap flights from Chicago. Every error fare is verified and bookable.
Source: Faro data, updated on 29/05/2026.

Key point: According to Faro data (2025), error fares offer an average 55% discount. Prices are verified every 30 minutes.

Deals active from Chicago

Cheap flights from Chicago. Every error fare is verified and bookable.
Price seen 9h ago -66%
Chicago (CHI) → 🇺🇸 Fort Lauderdale (FLL)
2 jul – 5 jul ·3 days
$82 $241
Book →
Price seen 9h ago -65%
Chicago (CHI) → 🇺🇸 Atlanta (ATL)
13 aoû – 18 aoû ·5 days
$56 $161
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Price seen 9h ago -62%
Chicago (CHI) → 🇺🇸 Myrtle Beach (MYR)
28 jul – 1 aoû ·4 days
$123 $323
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Price seen 9h ago -58%
Chicago (CHI) → 🇯🇲 Montego Bay (MBJ)
27 aoû – 1 sep ·5 days
$174 $412
Book →
Price seen 9h ago -58%
Chicago (CHI) → 🇨🇴 Cartagène (CTG)
1 jun – 5 jun ·4 days
$192 $455
Book →
PAE Price seen 9h ago -54%
Chicago (CHI) → 🇺🇸 Everett (PAE)
16 jun – 23 jun ·7 days
$153 $335
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Price seen 140h ago -54%
Chicago (CHI) → 🇩🇴 Punta Cana (PUJ)
4 oct – 14 oct ·10 days
$193 $408
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Price seen 9h ago -52%
Chicago (CHI) → 🇺🇸 Boston (BOS)
1 jun – 1 jun
$124 $260
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Price seen 9h ago -51%
Chicago (CHI) → 🇺🇸 Fairbanks (FAI)
15 jul – 24 jul ·9 days
$230 $467
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Price seen 9h ago -51%
Chicago (CHI) → 🇺🇸 Houston (HOU)
23 jun – 23 jun
$103 $208
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Price seen 9h ago -50%
Chicago (CHI) → 🇺🇸 New York (NYC)
16 jun – 23 jun ·7 days
$114 $227
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Price seen 9h ago -50%
Chicago (CHI) → 🇺🇸 Charlotte (CLT)
25 jul – 27 jul ·2 days
$132 $261
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Price seen 9h ago -50%
Chicago (CHI) → 🇺🇸 New York (NYC)
10 jun – 15 jun ·5 days
$112 $227
Book →
BUF Price seen 9h ago -50%
Chicago (CHI) → 🇺🇸 Buffalo (BUF)
24 jul – 25 jul ·1 days
$123 $245
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Price seen 9h ago -50%
Chicago (CHI) → 🇺🇸 New York (NYC)
27 aoû – 30 aoû ·3 days
$114 $227
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Price seen 9h ago -49%
Chicago (CHI) → 🇺🇸 Fort Lauderdale (FLL)
23 aoû – 29 aoû ·6 days
$122 $241
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Price seen 9h ago -48%
Chicago (CHI) → 🇲🇽 Cancun (CUN)
3 jul – 7 jul ·4 days
$176 $337
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Price seen 9h ago -48%
Chicago (CHI) → 🇲🇽 Mexico (MEX)
21 oct – 4 nov ·14 days
$157 $302
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Price seen 9h ago -47%
Chicago (CHI) → 🇺🇸 Baltimore (BWI)
15 jun – 17 jun ·2 days
$127 $242
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Price seen 9h ago -46%
Chicago (CHI) → 🇺🇸 Seattle (SEA)
16 jun – 23 jun ·7 days
$152 $284
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Price seen 9h ago -46%
Chicago (CHI) → 🇲🇽 Mexico (MEX)
10 jul – 14 jul ·4 days
$163 $302
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Price seen 9h ago -46%
Chicago (CHI) → 🇦🇼 Oranjestad (AUA)
10 jul – 12 jul ·2 days
$242 $451
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Price seen 9h ago -45%
Chicago (CHI) → 🇺🇸 Orlando (ORL)
22 jul – 27 jul ·5 days
$107 $193
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Price seen 9h ago -44%
Chicago (CHI) → 🇸🇻 Salvador (SAL)
20 jul – 2 aoû ·13 days
$208 $369
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Price seen 9h ago -44%
Chicago (CHI) → 🇲🇽 Guadalajara (GDL)
28 aoû – 22 sep ·25 days
$172 $309
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Price seen 9h ago -44%
Chicago (CHI) → 🇲🇽 Cancun (CUN)
16 oct – 19 oct ·3 days
$188 $337
Book →
Price seen 9h ago -43%
Chicago (CHI) → 🇺🇸 Fort Lauderdale (FLL)
22 aoû – 30 aoû ·8 days
$138 $241
Book →
Price seen 9h ago -42%
Chicago (CHI) → 🇺🇸 Washington (WAS)
15 jun – 17 jun ·2 days
$126 $218
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Price seen 9h ago -42%
Chicago (CHI) → 🇲🇽 Mexico (MEX)
28 oct – 3 nov ·6 days
$175 $302
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Price seen 9h ago -42%
Chicago (CHI) → 🇺🇸 Nashville (BNA)
9 jul – 12 jul ·3 days
$143 $246
Book →
PLN Price seen 9h ago -41%
Chicago (CHI) → 🇺🇸 Pellston (PLN)
31 jul – 3 aoû ·3 days
$440 $741
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Price seen 9h ago -41%
Chicago (CHI) → 🇺🇸 Seattle (SEA)
1 jun – 29 jun ·28 days
$168 $284
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Price seen 9h ago -41%
Chicago (CHI) → 🇵🇷 San Juan (SJU)
30 jun – 7 jul ·7 days
$157 $266
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Price seen 9h ago -41%
Chicago (CHI) → 🇺🇸 Nouvelle-Orléans (MSY)
17 jun – 20 jun ·3 days
$148 $251
Book →
Price seen 9h ago -41%
Chicago (CHI) → 🇺🇸 Philadelphie (PHL)
21 sep – 25 sep ·4 days
$123 $207
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Price seen 9h ago -40%
Chicago (CHI) → 🇲🇽 Mexico (MEX)
22 jun – 25 jun ·3 days
$183 $302
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Price seen 9h ago -40%
Chicago (CHI) → 🇺🇸 Los Angeles (LAX)
15 jul – 23 jul ·8 days
$140 $235
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Price seen 140h ago -40%
Chicago (CHI) → 🇺🇸 Minneapolis (MSP)
11 jul – 14 jul ·3 days
$146 $244
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Price seen 9h ago -40%
Chicago (CHI) → 🇲🇽 Cancun (CUN)
7 aoû – 11 aoû ·4 days
$201 $337
Book →
Price seen 9h ago -40%
Chicago (CHI) → 🇺🇸 Fort Lauderdale (FLL)
9 jun – 21 jun ·12 days
$145 $241
Book →
Price seen 9h ago -39%
Chicago (CHI) → 🇮🇳 Hyderabad (HYD)
22 aoû – 30 sep ·39 days
$725 $1,192
Book →
Price seen 9h ago -39%
Chicago (CHI) → 🇮🇳 Cochin (COK)
10 sep – 1 oct ·21 days
$859 $1,409
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Price seen 9h ago -38%
Chicago (CHI) → 🇺🇸 Miami (MIA)
19 aoû – 7 sep ·19 days
$133 $215
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Price seen 9h ago -38%
Chicago (CHI) → 🇺🇸 Orlando (ORL)
7 aoû – 10 aoû ·3 days
$120 $193
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Price seen 9h ago -38%
Chicago (CHI) → 🇺🇸 Las Vegas (LAS)
7 jul – 10 jul ·3 days
$140 $225
Book →
Price seen 9h ago -38%
Chicago (CHI) → 🇺🇸 Orlando (ORL)
13 aoû – 17 aoû ·4 days
$120 $193
Book →
Price seen 9h ago -37%
Chicago (CHI) → 🇺🇸 Boston (BOS)
13 jul – 14 jul ·1 days
$163 $260
Book →
Price seen 9h ago -37%
Chicago (CHI) → 🇨🇴 Cartagène (CTG)
2 jun – 7 jun ·5 days
$288 $455
Book →
Price seen 9h ago -37%
Chicago (CHI) → 🇲🇽 Guadalajara (GDL)
2 jun – 7 jul ·35 days
$193 $309
Book →
Price seen 9h ago -37%
Chicago (CHI) → 🇺🇸 Denver (DEN)
24 jul – 8 aoû ·15 days
$146 $232
Book →
Price seen 9h ago -36%
Chicago (CHI) → 🇺🇸 Dallas (DFW)
3 jun – 5 jun ·2 days
$136 $213
Book →
Price seen 140h ago -36%
Chicago (CHI) → 🇵🇱 Varsovie (WAW)
8 sep – 28 sep ·20 days
$459 $689
Book →
Price seen 9h ago -36%
Chicago (CHI) → 🇺🇸 Fort Lauderdale (FLL)
8 jun – 11 jun ·3 days
$154 $241
Book →
Price seen 9h ago -36%
Chicago (CHI) → 🇮🇳 Ahmedabad (AMD)
27 aoû – 17 sep ·21 days
$699 $1,090
Book →
Price seen 9h ago -35%
Chicago (CHI) → 🇨🇦 Toronto (YTO)
19 jun – 22 jun ·3 days
$177 $272
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇸 Houston (HOU)
24 jul – 27 jul ·3 days
$138 $208
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇩🇴 Punta Cana (PUJ)
26 jun – 30 jun ·4 days
$278 $420
Book →
Price seen 140h ago -34%
Chicago (CHI) → 🇵🇦 Panama (PTY)
20 jun – 27 jun ·7 days
$341 $500
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
1 sep – 30 oct ·59 days
$766 $1,158
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇸 Boston (BOS)
5 jun – 7 jun ·2 days
$172 $260
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇸 Newburgh (SWF)
10 jun – 13 jun ·3 days
$221 $335
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇸 Bradenton (SRQ)
15 aoû – 22 aoû ·7 days
$205 $310
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇬🇹 Guatemala (GUA)
9 oct – 13 oct ·4 days
$248 $377
Book →
Price seen 9h ago -34%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
1 oct – 15 oct ·14 days
$760 $1,158
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇸 Houston (HOU)
24 jun – 29 jun ·5 days
$139 $208
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
2 sep – 16 sep ·14 days
$778 $1,123
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
17 aoû – 8 sep ·22 days
$779 $1,158
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
10 nov – 10 déc ·30 days
$772 $1,158
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇸 Boston (BOS)
20 aoû – 23 aoû ·3 days
$174 $260
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇸 Las Vegas (LAS)
17 jul – 19 jul ·2 days
$150 $225
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇸 Boston (BOS)
13 jul – 28 jul ·15 days
$174 $260
Book →
Price seen 9h ago -33%
Chicago (CHI) → 🇺🇸 Tampa (TPA)
24 jun – 1 jul ·7 days
$146 $217
Book →
Price seen 9h ago -32%
Chicago (CHI) → 🇮🇹 Catane (CTA)
20 aoû – 24 aoû ·4 days
$696 $1,026
Book →
Price seen 9h ago -32%
Chicago (CHI) → 🇺🇸 Raleigh (RDU)
2 jul – 6 jul ·4 days
$127 $187
Book →
Price seen 140h ago -32%
Chicago (CHI) → 🇷🇸 Belgrade (BEG)
30 sep – 31 oct ·31 days
$596 $874
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇺🇸 Myrtle Beach (MYR)
22 jul – 28 jul ·6 days
$225 $323
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇺🇸 New York (NYC)
29 jul – 4 aoû ·6 days
$156 $227
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇰🇬 Bichkek (BSZ)
25 aoû – 21 oct ·57 days
$982 $1,431
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇰🇬 Bichkek (BSZ)
15 oct – 7 déc ·53 days
$993 $1,431
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇺🇸 Bradenton (SRQ)
3 jun – 10 jun ·7 days
$214 $310
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇺🇸 New York (NYC)
3 jul – 7 jul ·4 days
$157 $227
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇵🇱 Varsovie (WAW)
24 aoû – 8 sep ·15 days
$494 $712
Book →
Price seen 9h ago -31%
Chicago (CHI) → 🇲🇳 Oulan-Bator (UBN)
13 sep – 19 oct ·36 days
$943 $1,362
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇺🇸 Orlando (ORL)
10 jun – 17 jun ·7 days
$136 $193
Book →
Price seen 140h ago -30%
Chicago (CHI) → 🇲🇳 Oulan-Bator (UBN)
13 sep – 15 oct ·32 days
$950 $1,362
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇨🇴 Cartagène (CTG)
1 aoû – 6 aoû ·5 days
$319 $455
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇺🇸 Newburgh (SWF)
27 aoû – 30 aoû ·3 days
$233 $335
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇺🇸 Atlanta (ATL)
13 jul – 20 jul ·7 days
$113 $161
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇰🇬 Bichkek (BSZ)
28 sep – 10 nov ·43 days
$998 $1,431
Book →
Price seen 9h ago -30%
Chicago (CHI) → 🇺🇿 Tachkent (TAS)
18 aoû – 5 sep ·18 days
$815 $1,158
Book →
Price seen 9h ago -29%
Chicago (CHI) → 🇫🇷 Paris (PAR)
1 sep – 30 sep ·29 days
$543 $761
Book →
Price seen 9h ago -29%
Chicago (CHI) → 🇺🇸 Philadelphie (PHL)
22 jun – 26 jun ·4 days
$147 $207
Book →
Price seen 9h ago -29%
Chicago (CHI) → 🇺🇸 Long Beach (LGB)
10 oct – 17 oct ·7 days
$267 $376
Book →
Price seen 9h ago -29%
Chicago (CHI) → 🇺🇸 Houston (HOU)
1 sep – 1 sep
$148 $208
Book →
Price seen 9h ago -28%
Chicago (CHI) → 🇲🇽 Monterrey (MTY)
10 jun – 16 jun ·6 days
$227 $314
Book →
Price seen 9h ago -28%
Chicago (CHI) → 🇬🇪 Batoumi (BUS)
27 jul – 27 aoû ·31 days
$972 $1,356
Book →
Price seen 140h ago -28%
Chicago (CHI) → 🇲🇪 Tivat (TIV)
7 oct – 14 oct ·7 days
$773 $1,078
Book →
Price seen 9h ago -28%
Chicago (CHI) → 🇲🇽 Acapulco (ACA)
4 aoû – 14 aoû ·10 days
$314 $437
Book →
Price seen 9h ago -28%
Chicago (CHI) → 🇺🇸 Atlanta (ATL)
17 jun – 20 jun ·3 days
$116 $161
Book →
Price seen 9h ago -27%
Chicago (CHI) → 🇨🇳 Pekin (BJS)
30 sep – 14 oct ·14 days
$912 $1,243
Book →

Fare history

DateRoutePriceNormalOff
29/05/2026 Chicago → Astana $1,139 $1,277 -11%
29/05/2026 Chicago → Everett $474 $335 -0%
29/05/2026 Chicago → Bali $955 $1,302 -27%

See full history →

See also : All cheap flights · Error fare guide · Fare history