Live flight deals departing Chicago (O’Hare (ORD) · Midway (MDW)), each checked against its route's typical price wherever there is enough cached history to build one. Pipe this into any RSS reader, Slack or Telegram for free price alerts.https://flight.dealsen-ushttps://flight.deals/flights/chicago-to-orlando/#2026-12-04-2026-12-10-F9https://flight.deals/flights/chicago-to-orlando/#2026-12-04-2026-12-10-F9CHI → MCO round-trip on Frontier Airlines, 2026-12-04 to 2026-12-10 (6 nights). Cached fare $145 vs typical $230.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-washington/#2026-10-07-2026-11-03-WNhttps://flight.deals/flights/chicago-to-washington/#2026-10-07-2026-11-03-WNCHI → WAS round-trip on Southwest, 2026-10-07 to 2026-11-03 (27 nights). Cached fare $159. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-mexico-city/#2026-11-12-2026-11-16-AMhttps://flight.deals/flights/chicago-to-mexico-city/#2026-11-12-2026-11-16-AMCHI → MEX round-trip on Aeroméxico, 2026-11-12 to 2026-11-16 (4 nights). Cached fare $225. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-santo-domingo/#2026-09-05-2026-09-08-CMhttps://flight.deals/flights/chicago-to-santo-domingo/#2026-09-05-2026-09-08-CMCHI → SDQ round-trip on Copa Airlines, 2026-09-05 to 2026-09-08 (3 nights). Cached fare $354. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-punta-cana/#2027-05-11-2027-05-15-AAhttps://flight.deals/flights/chicago-to-punta-cana/#2027-05-11-2027-05-15-AACHI → PUJ round-trip on American, 2027-05-11 to 2027-05-15 (4 nights). Cached fare $404 vs typical $410.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-rome/#2027-02-15-2027-02-19-UAhttps://flight.deals/flights/chicago-to-rome/#2027-02-15-2027-02-19-UACHI → ROM round-trip on United, 2027-02-15 to 2027-02-19 (4 nights). Cached fare $410 vs typical $530.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-san-jose-costa-rica/#2027-04-08-2027-04-15-CMhttps://flight.deals/flights/chicago-to-san-jose-costa-rica/#2027-04-08-2027-04-15-CMCHI → SJO round-trip on Copa Airlines, 2027-04-08 to 2027-04-15 (7 nights). Cached fare $416. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-porto/#2027-04-03-2027-04-13-TPhttps://flight.deals/flights/chicago-to-porto/#2027-04-03-2027-04-13-TPCHI → OPO round-trip on TAP Air Portugal, 2027-04-03 to 2027-04-13 (10 nights). Cached fare $420. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-athens/#2026-10-26-2026-11-01-TKhttps://flight.deals/flights/chicago-to-athens/#2026-10-26-2026-11-01-TKCHI → ATH round-trip on Turkish Airlines, 2026-10-26 to 2026-11-01 (6 nights). Cached fare $422 vs typical $875.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-istanbul/#2026-10-21-2026-10-27-MShttps://flight.deals/flights/chicago-to-istanbul/#2026-10-21-2026-10-27-MSCHI → IST round-trip on EgyptAir, 2026-10-21 to 2026-10-27 (6 nights). Cached fare $486 vs typical $810.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-lisbon/#2026-11-20-2026-11-29-SKhttps://flight.deals/flights/chicago-to-lisbon/#2026-11-20-2026-11-29-SKCHI → LIS round-trip on SAS, 2026-11-20 to 2026-11-29 (9 nights). Cached fare $520 vs typical $820.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-frankfurt/#2026-11-20-2026-11-29-SKhttps://flight.deals/flights/chicago-to-frankfurt/#2026-11-20-2026-11-29-SKCHI → FRA round-trip on SAS, 2026-11-20 to 2026-11-29 (9 nights). Cached fare $528 vs typical $790.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-lima/#2026-11-24-2026-12-01-F9https://flight.deals/flights/chicago-to-lima/#2026-11-24-2026-12-01-F9CHI → LIM round-trip on Frontier Airlines, 2026-11-24 to 2026-12-01 (7 nights). Cached fare $583. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-bangkok/#2026-09-17-2026-10-09-EYhttps://flight.deals/flights/chicago-to-bangkok/#2026-09-17-2026-10-09-EYCHI → BKK round-trip on Etihad, 2026-09-17 to 2026-10-09 (22 nights). Cached fare $763 vs typical $965.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-jeddah/#2026-10-08-2026-10-29-EYhttps://flight.deals/flights/chicago-to-jeddah/#2026-10-08-2026-10-29-EYCHI → JED round-trip on Etihad, 2026-10-08 to 2026-10-29 (21 nights). Cached fare $774. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-tokyo/#2026-11-21-2026-11-29-UAhttps://flight.deals/flights/chicago-to-tokyo/#2026-11-21-2026-11-29-UACHI → TYO round-trip on United, 2026-11-21 to 2026-11-29 (8 nights). Cached fare $793 vs typical $985.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-doha/#2026-10-26-2026-11-02-EYhttps://flight.deals/flights/chicago-to-doha/#2026-10-26-2026-11-02-EYCHI → DOH round-trip on Etihad, 2026-10-26 to 2026-11-02 (7 nights). Cached fare $812. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-nairobi/#2026-11-22-2026-12-18-EYhttps://flight.deals/flights/chicago-to-nairobi/#2026-11-22-2026-12-18-EYCHI → NBO round-trip on Etihad, 2026-11-22 to 2026-12-18 (26 nights). Cached fare $863. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-kuala-lumpur/#2027-04-15-2027-04-22-EYhttps://flight.deals/flights/chicago-to-kuala-lumpur/#2027-04-15-2027-04-22-EYCHI → KUL round-trip on Etihad, 2027-04-15 to 2027-04-22 (7 nights). Cached fare $930. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-phuket/#2027-01-20-2027-02-03-CXhttps://flight.deals/flights/chicago-to-phuket/#2027-01-20-2027-02-03-CXCHI → HKT round-trip on Cathay Pacific, 2027-01-20 to 2027-02-03 (14 nights). Cached fare $943. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-bucharest/#2026-09-14-2026-09-18-SKhttps://flight.deals/flights/chicago-to-bucharest/#2026-09-14-2026-09-18-SKCHI → OTP round-trip on SAS, 2026-09-14 to 2026-09-18 (4 nights). Cached fare $969. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-marrakech/#2026-11-21-2026-12-12-TKhttps://flight.deals/flights/chicago-to-marrakech/#2026-11-21-2026-12-12-TKCHI → RAK round-trip on Turkish Airlines, 2026-11-21 to 2026-12-12 (21 nights). Cached fare $989. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-buenos-aires/#2027-04-08-2027-04-15-UAhttps://flight.deals/flights/chicago-to-buenos-aires/#2027-04-08-2027-04-15-UACHI → EZE round-trip on United, 2027-04-08 to 2027-04-15 (7 nights). Cached fare $1,144. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-maldives/#2026-12-24-2027-01-14-UAhttps://flight.deals/flights/chicago-to-maldives/#2026-12-24-2027-01-14-UACHI → MLE round-trip on United, 2026-12-24 to 2027-01-14 (21 nights). Cached fare $1,958. Not enough cached history on this route yet to say what it usually costs.Tue, 01 Sep 2026 12:09:07 GMThttps://flight.deals/flights/chicago-to-edinburgh/#2026-09-11-2026-09-14-FIhttps://flight.deals/flights/chicago-to-edinburgh/#2026-09-11-2026-09-14-FICHI → EDI round-trip on Icelandair, 2026-09-11 to 2026-09-14 (3 nights). Cached fare $870. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 10:38:54 GMThttps://flight.deals/flights/chicago-to-houston/#2026-09-17-2026-09-18-F9https://flight.deals/flights/chicago-to-houston/#2026-09-17-2026-09-18-F9CHI → HOU round-trip on Frontier Airlines, 2026-09-17 to 2026-09-18 (1 nights). Cached fare $140 vs typical $200.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-las-vegas/#2026-10-06-2026-10-10-WNhttps://flight.deals/flights/chicago-to-las-vegas/#2026-10-06-2026-10-10-WNCHI → LAS round-trip on Southwest, 2026-10-06 to 2026-10-10 (4 nights). Cached fare $145 vs typical $240.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-dallas/#2026-09-04-2026-09-08-F9https://flight.deals/flights/chicago-to-dallas/#2026-09-04-2026-09-08-F9CHI → DFW round-trip on Frontier Airlines, 2026-09-04 to 2026-09-08 (4 nights). Cached fare $148. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-cancun/#2026-09-07-2026-09-14-Y4https://flight.deals/flights/chicago-to-cancun/#2026-09-07-2026-09-14-Y4CHI → CUN round-trip on Volaris, 2026-09-07 to 2026-09-14 (7 nights). Cached fare $179 vs typical $365.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-oslo/#2026-11-15-2026-11-21-SKhttps://flight.deals/flights/chicago-to-oslo/#2026-11-15-2026-11-21-SKCHI → OSL round-trip on SAS, 2026-11-15 to 2026-11-21 (6 nights). Cached fare $261. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-honolulu/#2027-02-15-2027-02-18-WNhttps://flight.deals/flights/chicago-to-honolulu/#2027-02-15-2027-02-18-WNCHI → HNL round-trip on Southwest, 2027-02-15 to 2027-02-18 (3 nights). Cached fare $271 vs typical $675.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-san-juan/#2026-12-13-2026-12-19-AAhttps://flight.deals/flights/chicago-to-san-juan/#2026-12-13-2026-12-19-AACHI → SJU round-trip on American, 2026-12-13 to 2026-12-19 (6 nights). Cached fare $273. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-montreal/#2026-10-16-2026-10-18-P3https://flight.deals/flights/chicago-to-montreal/#2026-10-16-2026-10-18-P3CHI → YUL round-trip on Porter Airlines, 2026-10-16 to 2026-10-18 (2 nights). Cached fare $324. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-montego-bay/#2026-11-25-2026-11-30-UAhttps://flight.deals/flights/chicago-to-montego-bay/#2026-11-25-2026-11-30-UACHI → MBJ round-trip on United, 2026-11-25 to 2026-11-30 (5 nights). Cached fare $373 vs typical $800.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-cairo/#2026-11-04-2026-11-20-TKhttps://flight.deals/flights/chicago-to-cairo/#2026-11-04-2026-11-20-TKCHI → CAI round-trip on Turkish Airlines, 2026-11-04 to 2026-11-20 (16 nights). Cached fare $378 vs typical $445.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-madrid/#2027-03-08-2027-03-16-UAhttps://flight.deals/flights/chicago-to-madrid/#2027-03-08-2027-03-16-UACHI → MAD round-trip on United, 2027-03-08 to 2027-03-16 (8 nights). Cached fare $406 vs typical $705.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-geneva/#2027-04-19-2027-04-27-UAhttps://flight.deals/flights/chicago-to-geneva/#2027-04-19-2027-04-27-UACHI → GVA round-trip on United, 2027-04-19 to 2027-04-27 (8 nights). Cached fare $425. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-warsaw/#2026-10-05-2026-10-19-TKhttps://flight.deals/flights/chicago-to-warsaw/#2026-10-05-2026-10-19-TKCHI → WAW round-trip on Turkish Airlines, 2026-10-05 to 2026-10-19 (14 nights). Cached fare $438 vs typical $690.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-reykjavik/#2026-09-09-2026-09-16-FIhttps://flight.deals/flights/chicago-to-reykjavik/#2026-09-09-2026-09-16-FICHI → KEF round-trip on Icelandair, 2026-09-09 to 2026-09-16 (7 nights). Cached fare $442 vs typical $645.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-rio-de-janeiro/#2027-04-12-2027-04-20-AVhttps://flight.deals/flights/chicago-to-rio-de-janeiro/#2027-04-12-2027-04-20-AVCHI → RIO round-trip on Avianca, 2027-04-12 to 2027-04-20 (8 nights). Cached fare $473 vs typical $820.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-paris/#2027-06-04-2027-06-11-TPhttps://flight.deals/flights/chicago-to-paris/#2027-06-04-2027-06-11-TPCHI → PAR round-trip on TAP Air Portugal, 2027-06-04 to 2027-06-11 (7 nights). Cached fare $479 vs typical $620.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-manila/#2027-04-19-2027-04-27-UAhttps://flight.deals/flights/chicago-to-manila/#2027-04-19-2027-04-27-UACHI → MNL round-trip on United, 2027-04-19 to 2027-04-27 (8 nights). Cached fare $494 vs typical $670.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-amsterdam/#2026-09-08-2026-09-18-FIhttps://flight.deals/flights/chicago-to-amsterdam/#2026-09-08-2026-09-18-FICHI → AMS round-trip on Icelandair, 2026-09-08 to 2026-09-18 (10 nights). Cached fare $520. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-belgrade/#2026-09-04-2026-09-30-LOhttps://flight.deals/flights/chicago-to-belgrade/#2026-09-04-2026-09-30-LOCHI → BEG round-trip on LOT Polish, 2026-09-04 to 2026-09-30 (26 nights). Cached fare $588 vs typical $700.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-stockholm/#2026-10-24-2026-11-01-SKhttps://flight.deals/flights/chicago-to-stockholm/#2026-10-24-2026-11-01-SKCHI → STO round-trip on SAS, 2026-10-24 to 2026-11-01 (8 nights). Cached fare $592. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-tel-aviv/#2026-09-16-2026-10-09-EThttps://flight.deals/flights/chicago-to-tel-aviv/#2026-09-16-2026-10-09-ETCHI → TLV round-trip on Ethiopian, 2026-09-16 to 2026-10-09 (23 nights). Cached fare $616. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-barcelona/#2026-11-01-2026-11-08-TPhttps://flight.deals/flights/chicago-to-barcelona/#2026-11-01-2026-11-08-TPCHI → BCN round-trip on TAP Air Portugal, 2026-11-01 to 2026-11-08 (7 nights). Cached fare $630 vs typical $705.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-budapest/#2026-11-27-2026-12-05-SKhttps://flight.deals/flights/chicago-to-budapest/#2026-11-27-2026-12-05-SKCHI → BUD round-trip on SAS, 2026-11-27 to 2026-12-05 (8 nights). Cached fare $642. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-guangzhou/#2026-10-19-2026-10-24-UAhttps://flight.deals/flights/chicago-to-guangzhou/#2026-10-19-2026-10-24-UACHI → CAN round-trip on United, 2026-10-19 to 2026-10-24 (5 nights). Cached fare $646. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-seoul/#2027-03-23-2027-04-28-BRhttps://flight.deals/flights/chicago-to-seoul/#2027-03-23-2027-04-28-BRCHI → SEL round-trip on EVA Air, 2027-03-23 to 2027-04-28 (36 nights). Cached fare $647 vs typical $1,060.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-malaga/#2026-09-20-2026-10-30-TPhttps://flight.deals/flights/chicago-to-malaga/#2026-09-20-2026-10-30-TPCHI → AGP round-trip on TAP Air Portugal, 2026-09-20 to 2026-10-30 (40 nights). Cached fare $669. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-dubai/#2026-09-24-2026-10-07-RJhttps://flight.deals/flights/chicago-to-dubai/#2026-09-24-2026-10-07-RJCHI → DXB round-trip on Royal Jordanian, 2026-09-24 to 2026-10-07 (13 nights). Cached fare $677 vs typical $745.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-hamburg/#2026-09-25-2026-10-13-SKhttps://flight.deals/flights/chicago-to-hamburg/#2026-09-25-2026-10-13-SKCHI → HAM round-trip on SAS, 2026-09-25 to 2026-10-13 (18 nights). Cached fare $703. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-singapore/#2027-07-09-2027-08-20-KEhttps://flight.deals/flights/chicago-to-singapore/#2027-07-09-2027-08-20-KECHI → SIN round-trip on Korean Air, 2027-07-09 to 2027-08-20 (42 nights). Cached fare $738. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-brussels/#2026-09-21-2026-10-01-TKhttps://flight.deals/flights/chicago-to-brussels/#2026-09-21-2026-10-01-TKCHI → BRU round-trip on Turkish Airlines, 2026-09-21 to 2026-10-01 (10 nights). Cached fare $740. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-munich/#2026-09-24-2026-09-30-SKhttps://flight.deals/flights/chicago-to-munich/#2026-09-24-2026-09-30-SKCHI → MUC round-trip on SAS, 2026-09-24 to 2026-09-30 (6 nights). Cached fare $746. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-abu-dhabi/#2026-09-06-2026-09-30-RJhttps://flight.deals/flights/chicago-to-abu-dhabi/#2026-09-06-2026-09-30-RJCHI → AUH round-trip on Royal Jordanian, 2026-09-06 to 2026-09-30 (24 nights). Cached fare $771. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-delhi/#2026-11-06-2026-12-04-EYhttps://flight.deals/flights/chicago-to-delhi/#2026-11-06-2026-12-04-EYCHI → DEL round-trip on Etihad, 2026-11-06 to 2026-12-04 (28 nights). Cached fare $784. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-panama-city/#2026-09-11-2026-09-14-Y4https://flight.deals/flights/chicago-to-panama-city/#2026-09-11-2026-09-14-Y4CHI → PTY round-trip on Volaris, 2026-09-11 to 2026-09-14 (3 nights). Cached fare $789. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-sao-paulo/#2026-12-07-2026-12-19-DMhttps://flight.deals/flights/chicago-to-sao-paulo/#2026-12-07-2026-12-19-DMCHI → SAO round-trip on Arajet, 2026-12-07 to 2026-12-19 (12 nights). Cached fare $825. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-larnaca/#2026-12-29-2027-01-10-BAhttps://flight.deals/flights/chicago-to-larnaca/#2026-12-29-2027-01-10-BACHI → LCA round-trip on British Airways, 2026-12-29 to 2027-01-10 (12 nights). Cached fare $838. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-ho-chi-minh-city/#2026-11-04-2026-11-11-UAhttps://flight.deals/flights/chicago-to-ho-chi-minh-city/#2026-11-04-2026-11-11-UACHI → SGN round-trip on United, 2026-11-04 to 2026-11-11 (7 nights). Cached fare $856 vs typical $875.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-santiago/#2026-09-16-2026-10-15-F9https://flight.deals/flights/chicago-to-santiago/#2026-09-16-2026-10-15-F9CHI → SCL round-trip on Frontier Airlines, 2026-09-16 to 2026-10-15 (29 nights). Cached fare $856. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-hanoi/#2026-11-10-2026-11-21-EYhttps://flight.deals/flights/chicago-to-hanoi/#2026-11-10-2026-11-21-EYCHI → HAN round-trip on Etihad, 2026-11-10 to 2026-11-21 (11 nights). Cached fare $894. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-bali/#2026-10-08-2026-11-09-CXhttps://flight.deals/flights/chicago-to-bali/#2026-10-08-2026-11-09-CXCHI → DPS round-trip on Cathay Pacific, 2026-10-08 to 2026-11-09 (32 nights). Cached fare $938. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-beijing/#2026-09-13-2026-10-14-KEhttps://flight.deals/flights/chicago-to-beijing/#2026-09-13-2026-10-14-KECHI → PEK round-trip on Korean Air, 2026-09-13 to 2026-10-14 (31 nights). Cached fare $967 vs typical $985.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-hong-kong/#2026-11-04-2026-11-11-TKhttps://flight.deals/flights/chicago-to-hong-kong/#2026-11-04-2026-11-11-TKCHI → HKG round-trip on Turkish Airlines, 2026-11-04 to 2026-11-11 (7 nights). Cached fare $967 vs typical $1,120.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-zanzibar/#2026-09-25-2026-10-07-EYhttps://flight.deals/flights/chicago-to-zanzibar/#2026-09-25-2026-10-07-EYCHI → ZNZ round-trip on Etihad, 2026-09-25 to 2026-10-07 (12 nights). Cached fare $1,423. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-cape-town/#2026-12-29-2027-01-10-UAhttps://flight.deals/flights/chicago-to-cape-town/#2026-12-29-2027-01-10-UACHI → CPT round-trip on United, 2026-12-29 to 2027-01-10 (12 nights). Cached fare $2,053. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMThttps://flight.deals/flights/chicago-to-osaka/#2027-07-01-2027-07-15-CXhttps://flight.deals/flights/chicago-to-osaka/#2027-07-01-2027-07-15-CXCHI → KIX round-trip on Cathay Pacific, 2027-07-01 to 2027-07-15 (14 nights). Cached fare $1,417. Not enough cached history on this route yet to say what it usually costs.Mon, 24 Aug 2026 06:06:36 GMThttps://flight.deals/flights/chicago-to-seychelles/#2026-09-25-2026-10-07-TKhttps://flight.deals/flights/chicago-to-seychelles/#2026-09-25-2026-10-07-TKCHI → SEZ round-trip on Turkish Airlines, 2026-09-25 to 2026-10-07 (12 nights). Cached fare $1,452. Not enough cached history on this route yet to say what it usually costs.Mon, 24 Aug 2026 06:06:36 GMThttps://flight.deals/flights/chicago-to-mallorca/#2026-09-13-2026-09-19-BAhttps://flight.deals/flights/chicago-to-mallorca/#2026-09-13-2026-09-19-BACHI → PMI round-trip on British Airways, 2026-09-13 to 2026-09-19 (6 nights). Cached fare $680. Not enough cached history on this route yet to say what it usually costs.Sun, 23 Aug 2026 05:58:32 GMThttps://flight.deals/flights/chicago-to-johannesburg/#2026-09-11-2026-09-19-QRhttps://flight.deals/flights/chicago-to-johannesburg/#2026-09-11-2026-09-19-QRCHI → JNB round-trip on Qatar Airways, 2026-09-11 to 2026-09-19 (8 nights). Cached fare $1,399. Not enough cached history on this route yet to say what it usually costs.Sun, 23 Aug 2026 05:58:32 GMThttps://flight.deals/flights/chicago-to-shanghai/#2026-09-16-2026-09-30-CXhttps://flight.deals/flights/chicago-to-shanghai/#2026-09-16-2026-09-30-CXCHI → SHA round-trip on Cathay Pacific, 2026-09-16 to 2026-09-30 (14 nights). Cached fare $974. Not enough cached history on this route yet to say what it usually costs.Fri, 21 Aug 2026 06:01:13 GMThttps://flight.deals/flights/chicago-to-venice/#2026-12-18-2027-01-02-AChttps://flight.deals/flights/chicago-to-venice/#2026-12-18-2027-01-02-ACCHI → VCE round-trip on Air Canada, 2026-12-18 to 2027-01-02 (15 nights). Cached fare $1,478. Not enough cached history on this route yet to say what it usually costs.Fri, 21 Aug 2026 06:01:13 GMThttps://flight.deals/flights/chicago-to-alicante/#2026-10-01-2026-10-22-FIhttps://flight.deals/flights/chicago-to-alicante/#2026-10-01-2026-10-22-FICHI → ALC round-trip on Icelandair, 2026-10-01 to 2026-10-22 (21 nights). Cached fare $851. Not enough cached history on this route yet to say what it usually costs.Tue, 18 Aug 2026 05:58:04 GMThttps://flight.deals/flights/chicago-to-colombo/#2027-01-11-2027-01-24-EYhttps://flight.deals/flights/chicago-to-colombo/#2027-01-11-2027-01-24-EYCHI → CMB round-trip on Etihad, 2027-01-11 to 2027-01-24 (13 nights). Cached fare $1,115. Not enough cached history on this route yet to say what it usually costs.Tue, 18 Aug 2026 05:58:04 GMThttps://flight.deals/flights/chicago-to-ibiza/#2027-06-01-2027-06-08-BAhttps://flight.deals/flights/chicago-to-ibiza/#2027-06-01-2027-06-08-BACHI → IBZ round-trip on British Airways, 2027-06-01 to 2027-06-08 (7 nights). Cached fare $906. Not enough cached history on this route yet to say what it usually costs.Mon, 17 Aug 2026 06:03:15 GMThttps://flight.deals/flights/chicago-to-sydney/#2026-11-07-2026-12-04-UAhttps://flight.deals/flights/chicago-to-sydney/#2026-11-07-2026-12-04-UACHI → SYD round-trip on United, 2026-11-07 to 2026-12-04 (27 nights). Cached fare $923. Not enough cached history on this route yet to say what it usually costs.Mon, 17 Aug 2026 06:03:15 GMThttps://flight.deals/flights/chicago-to-bogota/#2026-10-18-2026-10-25-AAhttps://flight.deals/flights/chicago-to-bogota/#2026-10-18-2026-10-25-AACHI → BOG round-trip on American, 2026-10-18 to 2026-10-25 (7 nights). Cached fare $424. Not enough cached history on this route yet to say what it usually costs.Sat, 15 Aug 2026 22:25:30 GMThttps://flight.deals/flights/chicago-to-prague/#2026-09-28-2026-10-04-TKhttps://flight.deals/flights/chicago-to-prague/#2026-09-28-2026-10-04-TKCHI → PRG round-trip on Turkish Airlines, 2026-09-28 to 2026-10-04 (6 nights). Cached fare $801. Not enough cached history on this route yet to say what it usually costs.Sat, 15 Aug 2026 22:25:30 GMThttps://flight.deals/flights/chicago-to-melbourne/#2026-11-07-2026-12-05-NZhttps://flight.deals/flights/chicago-to-melbourne/#2026-11-07-2026-12-05-NZCHI → MEL round-trip on Air New Zealand, 2026-11-07 to 2026-12-05 (28 nights). Cached fare $802. Not enough cached history on this route yet to say what it usually costs.Sat, 15 Aug 2026 22:25:30 GMThttps://flight.deals/flights/chicago-to-mauritius/#2026-09-09-2026-09-16-AFhttps://flight.deals/flights/chicago-to-mauritius/#2026-09-09-2026-09-16-AFCHI → MRU round-trip on Air France, 2026-09-09 to 2026-09-16 (7 nights). Cached fare $1,575. Not enough cached history on this route yet to say what it usually costs.Sat, 08 Aug 2026 12:21:11 GMThttps://flight.deals/flights/chicago-to-auckland/#2026-11-07-2026-11-14-B6https://flight.deals/flights/chicago-to-auckland/#2026-11-07-2026-11-14-B6CHI → AKL round-trip on JetBlue, 2026-11-07 to 2026-11-14 (7 nights). Cached fare $1,429. Not enough cached history on this route yet to say what it usually costs.Wed, 05 Aug 2026 07:53:34 GMT