Stopover flights from Chicago: 16 cities to visit
Trips from Chicago with a stop long enough to leave the airport, through 16 cities. Each price is for the whole trip, the stop included.
A stop here is at least 8 hours in the daytime, or at least 18 hours when it runs overnight, and at most 24 hours. It is in the same airport, on the way to where you are going, and never on a trip we think is on separate tickets. Leaving the airport means entering that country, so check its entry rules for your passport.
Stop in Istanbul
32 trips go through Istanbul. The best are here.
Tashkent · one-way
$621
8 h 35 min in Istanbul (IST) on the way there
31 Mar 2027 · ORD → TAS · United Airlines
2 stops · in with Lufthansa, out with Uzbekistan Airways
$9 more than the cheapest fare without a long stop on the same dates
found 6 days ago
Astana · one-way
$736
10 h 15 min in Istanbul (IST) on the way there
6 Sept 2027 · ORD → NQZ · Turkish Airlines
1 stop · Turkish Airlines both into and out of the stop
$135 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Dubai · return
$750
9 h 25 min in Istanbul (IST) on the way there
9 Feb 2027 – 23 Feb 2027 · ORD → DXB · Turkish Airlines
out 1 stop, back 1 stop · Turkish Airlines both into and out of the stop
The same price as the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Atlanta
20 trips go through Atlanta. The best are here.
Washington · one-way
$94
13 h 5 min in Atlanta (ATL) on the way there
16 Feb 2027 · ORD → IAD · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$19 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Baltimore · one-way
$98
13 h 18 min in Atlanta (ATL) on the way there
10 Feb 2027 · ORD → BWI · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$8 less than the cheapest fare without a long stop on the same dates
found 5 days ago
Orlando · one-way
$125
10 h 1 min in Atlanta (ATL) on the way there
29 Dec · ORD → MCO · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$9 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Miami · one-way
$147
20 h 10 min in Atlanta (ATL) on the way there · overnight connection
1 Dec · ORD → MIA · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$55 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Orlando · return
$220
22 h 28 min in Atlanta (ATL) on the way back · overnight connection
11 Dec – 14 Dec · ORD → MCO · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$44 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Warsaw
15 trips go through Warsaw. The best are here.
Istanbul · one-way
$802
10 h 50 min in Warsaw (WAW) on the way there
16 May 2027 · ORD → IST · LOT Polish
1 stop · LOT Polish both into and out of the stop
$342 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Chisinau · return
$722
21 h 10 min in Warsaw (WAW) on the way there · overnight connection
5 Mar 2027 – 10 Mar 2027 · ORD → RMO · LOT Polish
out 1 stop, back 1 stop · LOT Polish both into and out of the stop
$61 less than the cheapest fare without a long stop on the same dates
found 3 days ago
Almaty · return
$1,441
8 h 45 min in Warsaw (WAW) on the way there
31 Mar 2027 – 10 Apr 2027 · ORD → ALA · LOT Polish
out 1 stop, back 2 stops · LOT Polish both into and out of the stop
$470 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Yerevan · return
$1,459
8 h 55 min in Warsaw (WAW) on the way back
1 Dec – 15 Jan 2027 · ORD → EVN · Turkish Airlines
out 1 stop, back 1 stop · LOT Polish both into and out of the stop
$398 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Istanbul · return
$2,016
22 h 55 min in Warsaw (WAW) on the way there · overnight connection
17 Dec – 5 Jan 2027 · ORD → IST · LOT Polish
out 1 stop, back 2 stops · LOT Polish both into and out of the stop
$205 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Abu Dhabi
14 trips go through Abu Dhabi. The best are here.
Tashkent · one-way
$633
8 h 35 min in Abu Dhabi (AUH) on the way there
28 Jan 2027 · ORD → TAS · Etihad Airways
1 stop · Etihad Airways both into and out of the stop
$57 less than the cheapest fare without a long stop on the same dates
found 3 days ago
Karachi · one-way
$685
11 h 10 min in Abu Dhabi (AUH) on the way there
17 Oct 2027 · ORD → KHI · Etihad Airways
1 stop · Etihad Airways both into and out of the stop
$23 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Hong Kong · one-way
$703
8 h 40 min in Abu Dhabi (AUH) on the way there
24 Sept 2027 · ORD → HKG · Etihad Airways
1 stop · Etihad Airways both into and out of the stop
$180 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Tashkent · return
$829
20 h in Abu Dhabi (AUH) on the way back · overnight connection
31 Jan 2027 – 10 Mar 2027 · ORD → TAS · Etihad Airways
out 1 stop, back 1 stop · Etihad Airways both into and out of the stop
$72 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Munich
12 trips go through Munich. The best are here.
Istanbul · one-way
$361
9 h 20 min in Munich (MUC) on the way there · connection may need a visa
12 May 2027 · ORD → IST · Lufthansa
1 stop · Lufthansa both into and out of the stop
$550 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Moscow · one-way
$664
9 h 20 min in Munich (MUC) on the way there
27 Sept 2027 · ORD → VKO · Lufthansa
2 stops · Lufthansa both into and out of the stop
$123 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Moscow · return
$2,145
9 h in Munich (MUC) on the way there
22 Dec – 10 Jan 2027 · ORD → ZIA · Lufthansa
out 2 stops, back 2 stops · Lufthansa both into and out of the stop
$29 more than the cheapest fare without a long stop on the same dates
found yesterday
Warsaw · return
$928
8 h 5 min in Munich (MUC) on the way back
2 Dec – 28 Dec · ORD → WAW · Lufthansa
out 1 stop, back 1 stop · in with United Airlines, out with Lufthansa
The same price as the cheapest fare without a long stop on the same dates
found 2 days ago
Vilnius · return
$1,137
19 h 30 min in Munich (MUC) on the way there · overnight connection
1 Dec – 23 Dec · ORD → VNO · Lufthansa
out 1 stop, back 1 stop · in with Lufthansa, out with airBaltic
$385 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Denver
10 trips go through Denver. The best are here.
Ontario · one-way
$125
14 h 19 min in Denver (DEN) on the way there
25 Jan 2027 · ORD → ONT · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$10 less than the cheapest fare without a long stop on the same dates
found 3 days ago
Las Vegas · one-way
$148
10 h 47 min in Denver (DEN) on the way there
10 Feb 2027 · ORD → LAS · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$47 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Los Angeles · one-way
$150
13 h in Denver (DEN) on the way there
7 Dec · ORD → LAX · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$28 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Las Vegas · return
$184
13 h 21 min in Denver (DEN) on the way there
5 Dec – 6 Dec · ORD → LAS · Frontier Airlines
out 1 stop, back nonstop · Frontier Airlines both into and out of the stop
$78 less than the cheapest fare without a long stop on the same dates
found 2 days ago
San Diego · return
$283
13 h 27 min in Denver (DEN) on the way there
3 Dec – 11 Dec · ORD → SAN · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$89 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Toronto
9 trips go through Toronto. The best are here.
Washington · one-way
$518
18 h 15 min in Toronto (YTZ) on the way there · overnight connection · connection may need a visa
16 Feb 2027 · ORD → IAD · Porter Airlines Canada
1 stop · in with Porter Airlines Canada, out with Air Canada
$443 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Las Vegas · one-way
$646
20 h 58 min in Toronto (YYZ) on the way there · overnight connection · connection may need a visa
10 Feb 2027 · ORD → LAS · Porter Airlines Canada
1 stop · in with Air Canada, out with Porter Airlines Canada
$545 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Hong Kong · one-way
$1,146
12 h 59 min in Toronto (YYZ) on the way there · connection may need a visa
24 Sept 2027 · ORD → HKG · Air Canada
3 stops · Air Canada both into and out of the stop
$623 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Paris · return
$778
21 h 11 min in Toronto (YYZ) on the way there · overnight connection
13 Feb 2027 – 20 Feb 2027 · ORD → CDG · American Airlines
out 1 stop, back 1 stop · United Airlines both into and out of the stop
$140 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Rio de Janeiro · return
$1,034
13 h 20 min in Toronto (YYZ) on the way back · connection may need a visa
18 Nov – 26 Nov · ORD → GIG · Air Canada
out 1 stop, back 1 stop · Air Canada both into and out of the stop
$201 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Stop in Stockholm
8 trips go through Stockholm. The best are here.
Istanbul · one-way
$421
9 h in Stockholm (ARN) on the way there
17 Jan 2027 · ORD → IST · Icelandair
3 stops · in with Icelandair, out with Air Serbia
$78 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Belgrade · return
$1,160
22 h in Stockholm (ARN) on the way there · overnight connection · connection may need a visa
14 Jan 2027 – 15 Feb 2027 · ORD → BEG · Icelandair
out 2 stops, back 2 stops · in with Icelandair, out with Air Serbia
$373 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Berlin · return
$615
19 h 45 min in Stockholm (ARN) on the way there · overnight connection
1 Feb 2027 – 10 Feb 2027 · ORD → BER · SAS Scandinavian
out 2 stops, back 1 stop · SAS Scandinavian both into and out of the stop
$185 less than the cheapest fare without a long stop on the same dates
found 6 days ago
Istanbul · return
$794
23 h 35 min in Stockholm (ARN) on the way there · overnight connection
16 Nov – 25 Nov · ORD → IST · Icelandair
out 2 stops, back 2 stops · in with Icelandair, out with Turkish Airlines
$115 more than the cheapest fare without a long stop on the same dates
found 6 days ago
Stop in Belgrade
7 trips go through Belgrade. The best are here.
Moscow · one-way
$1,077
12 h 35 min in Belgrade (BEG) on the way there
31 May 2027 · ORD → SVO · Air Serbia
1 stop · Air Serbia both into and out of the stop
$137 less than the cheapest fare without a long stop on the same dates
found 6 days ago
Istanbul · return
$1,159
8 h 55 min in Belgrade (BEG) on the way there
22 May 2027 – 30 Jun 2027 · ORD → IST · Air Serbia
out 1 stop, back 1 stop · Air Serbia both into and out of the stop
$310 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Milan · return
$769
8 h 55 min in Belgrade (BEG) on the way there
31 Mar 2027 – 7 Apr 2027 · ORD → MXP · Air Serbia
out 1 stop, back 1 stop · Air Serbia both into and out of the stop
$68 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Zurich · return
$945
20 h 30 min in Belgrade (BEG) on the way there · overnight connection
9 Jan 2027 – 16 Jan 2027 · ORD → ZRH · Air Serbia
out 1 stop, back 1 stop · Air Serbia both into and out of the stop
$182 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Novosibirsk · return
$2,153
8 h 5 min in Belgrade (BEG) on the way there
23 Dec – 24 Jan 2027 · ORD → OVB · Turkish Airlines
out 2 stops, back 2 stops · Air Serbia both into and out of the stop
No fare on this route without a long stop to compare with
found 4 days ago
Stop in Boston
6 trips go through Boston. The best are here.
Istanbul · one-way
$447
8 h 21 min in Boston (BOS) on the way there
16 May 2027 · ORD → IST · United Airlines
2 stops · in with United Airlines, out with Lufthansa
$13 less than the cheapest fare without a long stop on the same dates
found 6 days ago
Tashkent · return
$1,035
20 h 45 min in Boston (BOS) on the way back · overnight connection
28 Jan 2027 – 16 Feb 2027 · ORD → TAS · Qatar Airways
out 1 stop, back 2 stops · in with Qatar Airways, out with jetBlue
$382 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Paris · return
$1,384
23 h 1 min in Boston (BOS) on the way there · overnight connection
10 Dec – 19 Dec · ORD → CDG · jetBlue
out 1 stop, back 1 stop · jetBlue both into and out of the stop
$433 more than the cheapest fare without a long stop on the same dates
found 2 days ago
London · return
$944
19 h 40 min in Boston (BOS) on the way back · overnight connection
14 Nov – 21 Nov · ORD → LHR · jetBlue
out 1 stop, back 1 stop · jetBlue both into and out of the stop
$56 less than the cheapest fare without a long stop on the same dates
found 5 days ago
Istanbul · return
$1,688
9 h in Boston (BOS) on the way there
27 Dec – 5 Jan 2027 · MDW → IST · LOT Polish
out 1 stop, back 1 stop · in with Southwest Airlines, out with Turkish Airlines
$243 more than the cheapest fare without a long stop on the same dates
found 7 days ago
Stop in Copenhagen
15 trips go through Copenhagen. The best are here.
Vilnius · return
$672
12 h 35 min in Copenhagen (CPH) on the way there
1 Dec – 23 Dec · ORD → VNO · SAS Scandinavian
out 1 stop, back 1 stop · SAS Scandinavian both into and out of the stop
$80 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Krakow · return
$777
21 h 30 min in Copenhagen (CPH) on the way there · overnight connection
30 Dec – 10 Jan 2027 · ORD → KRK · SAS Scandinavian
out 1 stop, back 2 stops · SAS Scandinavian both into and out of the stop
$26 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Amsterdam · return
$806
22 h 5 min in Copenhagen (CPH) on the way there · overnight connection
8 Sept 2027 – 18 Sept 2027 · ORD → AMS · SAS Scandinavian
out 1 stop, back 1 stop · SAS Scandinavian both into and out of the stop
$16 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Paris · return
$925
21 h 5 min in Copenhagen (CPH) on the way back · overnight connection
10 Dec – 19 Dec · ORD → CDG · SAS Scandinavian
out 1 stop, back 1 stop · SAS Scandinavian both into and out of the stop
$26 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Yerevan · return
$1,257
23 h in Copenhagen (CPH) on the way there · overnight connection · connection may need a visa
1 Dec – 16 Jan 2027 · ORD → EVN · Icelandair
out 3 stops, back 3 stops · in with Icelandair, out with Pegasus Airlines
$152 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Frankfurt
11 trips go through Frankfurt. The best are here.
Cairo · return
$1,194
9 h 25 min in Frankfurt (FRA) on the way there
1 Jun 2027 – 4 Jul 2027 · ORD → CAI · Condor
out 1 stop, back 2 stops · Condor both into and out of the stop
$229 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Istanbul · return
$2,079
10 h 5 min in Frankfurt (FRA) on the way there
17 Dec – 5 Jan 2027 · ORD → IST · Lufthansa
out 1 stop, back 1 stop · Lufthansa both into and out of the stop
$268 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Belgrade · return
$890
9 h 30 min in Frankfurt (FRA) on the way back
17 Nov – 23 Dec · ORD → BEG · Lufthansa
out 1 stop, back 1 stop · Lufthansa both into and out of the stop
$13 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Tallinn · return
$1,323
9 h 50 min in Frankfurt (FRA) on the way back
1 Jul 2027 – 21 Jul 2027 · ORD → TLL · Lufthansa
out 1 stop, back 1 stop · Lufthansa both into and out of the stop
$289 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Saint Petersburg · return
$1,566
8 h in Frankfurt (FRA) on the way there
8 Dec – 28 Jan 2027 · ORD → LED · Turkish Airlines
out 2 stops, back 1 stop · in with United Airlines, out with Lufthansa
$205 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Stop in Paris
10 trips go through Paris. The best are here.
Almaty · return
$1,624
19 h 25 min in Paris (CDG) on the way back · overnight connection
25 Dec – 10 Jan 2027 · MDW → ALA · Virgin Atlantic
out 3 stops, back 3 stops · in with SunExpress, out with Aer Lingus
$684 more than the cheapest fare without a long stop on this route (6 Jan 2027 – 28 Jan 2027)
found 2 days ago
Cairo · return
$846
10 h 40 min in Paris (CDG) on the way there
9 Jan 2027 – 16 Jan 2027 · ORD → CAI · Air France
out 1 stop, back 1 stop · Air France both into and out of the stop
$84 less than the cheapest fare without a long stop on the same dates
found 6 days ago
Dubai · return
$928
22 h 25 min in Paris (CDG) on the way back · overnight connection
8 Dec – 27 Dec · ORD → DXB · Air France
out 1 stop, back 1 stop · Air France both into and out of the stop
$301 less than the cheapest fare without a long stop on the same dates
found 5 days ago
Stop in Houston
9 trips go through Houston. The best are here.
Phoenix · return
$408
10 h 24 min in Houston (IAH) on the way there
20 Nov – 24 Nov · ORD → PHX · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$28 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Tampa · return
$435
11 h 58 min in Houston (IAH) on the way back
16 Jan 2027 – 21 Jan 2027 · ORD → TPA · Frontier Airlines
out nonstop, back 1 stop · Frontier Airlines both into and out of the stop
$256 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Miami · return
$389
8 h 55 min in Houston (IAH) on the way back
5 Feb 2027 – 19 Feb 2027 · ORD → MIA · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$176 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Mexico City · return
$608
11 h 12 min in Houston (IAH) on the way there
13 Dec – 18 Jan 2027 · ORD → MEX · Aeromexico
out 1 stop, back nonstop · United Airlines both into and out of the stop
$75 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Rio de Janeiro · return
$1,027
21 h 23 min in Houston (IAH) on the way there · overnight connection
21 Jan 2027 – 26 Jan 2027 · ORD → GIG · United Airlines
out 1 stop, back 2 stops · United Airlines both into and out of the stop
$300 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Stop in Cairo
8 trips go through Cairo. The best are here.
Dubai · return
$1,344
19 h 45 min in Cairo (CAI) on the way back
3 Jan 2027 – 10 Jan 2027 · ORD → DXB · Egyptair
out 1 stop, back 1 stop · Egyptair both into and out of the stop
$66 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Bishkek · return
$1,974
10 h 15 min in Cairo (CAI) on the way back · connection may need a visa
2 Dec – 25 Dec · ORD → BSZ · Egyptair
out 2 stops, back 2 stops · in with Air Arabia Egypt, out with Egyptair
$760 more than the cheapest fare without a long stop on this route (2 Dec – 24 Dec)
found 2 days ago
Tashkent · return
$1,429
8 h 55 min in Cairo (CAI) on the way there · connection may need a visa
18 Nov – 15 Jan 2027 · ORD → TAS · Egyptair
out 2 stops, back 3 stops · in with Egyptair, out with Turkish Airlines
$356 less than the cheapest fare without a long stop on the same dates
found 5 days ago
Yerevan · return
$1,521
9 h 30 min in Cairo (CAI) on the way back
1 Dec – 17 Jan 2027 · ORD → EVN · Egyptair
out 1 stop, back 2 stops · Egyptair both into and out of the stop
$564 more than the cheapest fare without a long stop on this route (2 Jan 2027 – 13 Jan 2027)
found 4 days ago
Stop in Los Angeles
7 trips go through Los Angeles. The best are here.
Manila · return
$836
11 h 45 min in Los Angeles (LAX) on the way back
15 Feb 2027 – 1 Mar 2027 · MDW → MNL · Southwest Airlines
out 1 stop, back 1 stop · in with Philippine Airlines, out with Southwest Airlines
$16 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Bangkok · return
$1,084
10 h 10 min in Los Angeles (LAX) on the way back
22 Jan 2027 – 31 Jan 2027 · ORD → BKK · Philippine Airlines
out 1 stop, back 2 stops · in with Korean Air, out with Southwest Airlines
$404 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Dipolog · return
$1,248
9 h 10 min in Los Angeles (LAX) on the way there
31 May 2027 – 12 Jul 2027 · MDW → DPL · Southwest Airlines
out 2 stops, back 2 stops · in with Southwest Airlines, out with Philippine Airlines
$405 less than the cheapest fare without a long stop on the same dates
found 2 days ago
Las Vegas · return
$333
10 h 18 min in Los Angeles (LAX) on the way there
18 Dec – 20 Dec · ORD → LAS · Frontier Airlines
out 1 stop, back nonstop · Frontier Airlines both into and out of the stop
$11 less than the cheapest fare without a long stop on the same dates
found 4 days ago
San Francisco · return
$669
18 h 28 min in Los Angeles (LAX) on the way there · overnight connection
22 Dec – 27 Dec · MDW → SFO · Frontier Airlines
out 2 stops, back 1 stop · Frontier Airlines both into and out of the stop
$309 more than the cheapest fare without a long stop on the same dates
found 6 days ago
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work