Stopovers from Chicago
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 Atlanta
6 trips go through Atlanta. The best are here.
Orlando · one-way
$85
9 h 51 min in Atlanta (ATL) on the way there
12 Jan 2027 · ORD → MCO · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$10 more than the cheapest fare without a long stop on the same dates
found yesterday
Fort Lauderdale · one-way
$119
22 h in Atlanta (ATL) on the way there · overnight connection
15 Nov · MDW → FLL · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$65 more than the cheapest fare without a long stop on the same dates
found 3 days ago
New York · return
$336
10 h 42 min in Atlanta (ATL) on the way there
3 Dec – 6 Dec · ORD → EWR · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$52 more than the cheapest fare without a long stop on the same dates
found 18 hours ago
New York · one-way
$578
9 h 26 min in Atlanta (ATL) on the way there
20 Oct · MDW → EWR · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$444 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Fort Lauderdale · return
$227
8 h 6 min in Atlanta (ATL) on the way back
1 Nov – 5 Nov · ORD → FLL · Frontier Airlines
out nonstop, back 1 stop · Frontier Airlines both into and out of the stop
$154 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Istanbul
5 trips go through Istanbul. The best are here.
Bishkek · return
$1,024
9 h 20 min in Istanbul (IST) on the way there
29 Nov – 5 Dec · ORD → BSZ · Turkish Airlines
out 1 stop, back 1 stop · Turkish Airlines both into and out of the stop
$1,359 less than the cheapest fare without a long stop on the same dates
found 23 hours ago
Moscow · one-way
$1,055
12 h 30 min in Istanbul (IST) on the way there
6 Jan 2027 · ORD → VKO · Turkish Airlines
1 stop · in with Turkish Airlines, out with Pobeda
$310 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Tashkent · return
$1,126
14 h 40 min in Istanbul (IST) on the way there
26 Nov – 30 Dec · ORD → TAS · 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 6 hours ago
Moscow · return
$2,155
9 h 10 min in Istanbul (IST) on the way there
6 Nov – 11 Nov · ORD → DME · Egyptair
out 1 stop, back 1 stop · in with Turkish Airlines, out with Ural Airlines
$785 more than the cheapest fare without a long stop on the same dates
found 17 hours ago
Bishkek · one-way
$2,616
10 h 15 min in Istanbul (IST) on the way there
6 Apr 2027 · MDW → BSZ · Turkish Airlines
3 stops · Turkish Airlines both into and out of the stop
$2,032 more than the cheapest fare without a long stop on the same dates
found 23 hours ago
Stop in Denver
3 trips go through Denver. The best are here.
Los Angeles · one-way
$175
13 h 44 min in Denver (DEN) on the way there
31 Dec · ORD → LAX · Frontier Airlines
1 stop · Frontier Airlines both into and out of the stop
$12 more than the cheapest fare without a long stop on the same dates
found 23 hours ago
Las Vegas · return
$474
21 h 18 min in Denver (DEN) on the way there · overnight connection
19 Dec – 26 Dec · ORD → LAS · Frontier Airlines
out 1 stop, back nonstop · Frontier Airlines both into and out of the stop
$235 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Los Angeles · return
$288
11 h 20 min in Denver (DEN) on the way back
20 Nov – 27 Nov · ORD → LAX · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$45 more than the cheapest fare without a long stop on the same dates
found 7 days ago
Stop in Warsaw
3 trips go through Warsaw. The best are here.
Istanbul · return
$814
19 h 15 min in Warsaw (WAW) on the way there · overnight connection
12 Feb 2027 – 21 Feb 2027 · ORD → IST · LOT Polish
out 1 stop, back 1 stop · LOT Polish both into and out of the stop
$69 more than the cheapest fare without a long stop on the same dates
found 21 hours ago
Tashkent · one-way
$1,345
8 h 45 min in Warsaw (WAW) on the way there
26 Jul 2027 · ORD → TAS · LOT Polish
2 stops · LOT Polish both into and out of the stop
$720 more than the cheapest fare without a long stop on the same dates
found 19 hours ago
Tashkent · return
$1,417
9 h 5 min in Warsaw (WAW) on the way there
20 Mar 2027 – 21 Apr 2027 · ORD → TAS · LOT Polish
out 1 stop, back 2 stops · LOT Polish both into and out of the stop
$294 more than the cheapest fare without a long stop on the same dates
found 6 days ago
Stop in Knoxville
2 trips go through Knoxville. The best are here.
New York · one-way
$697
20 h 6 min in Knoxville (TYS) on the way there · overnight connection
27 Nov · RFD → EWR · Allegiant Air
2 stops · Allegiant Air both into and out of the stop
$541 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Orlando · return
$345
19 h 9 min in Knoxville (TYS) on the way there · overnight connection
30 Oct – 2 Nov · MDW → SFB · Allegiant Air
out 1 stop, back nonstop · Allegiant Air both into and out of the stop
$106 more than the cheapest fare without a long stop on the same dates
found 3 days ago
Stop in Toronto
2 trips go through Toronto. The best are here.
New York · one-way
$628
8 h 18 min in Toronto (YYZ) on the way there · connection may need a visa
27 Nov · ORD → EWR · Air Canada
1 stop · Air Canada both into and out of the stop
$472 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Tashkent · return
$1,374
21 h 6 min in Toronto (YYZ) on the way back · overnight connection · connection may need a visa
26 Oct – 4 Dec · ORD → TAS · Qatar Airways
out 2 stops, back 2 stops · Qatar Airways both into and out of the stop
$296 less than the cheapest fare without a long stop on the same dates
found 4 days ago
Stop in Abu Dhabi
2 trips go through Abu Dhabi. The best are here.
Tashkent · one-way
$660
8 h 40 min in Abu Dhabi (AUH) on the way there
26 Jul 2027 · ORD → TAS · Etihad Airways
1 stop · Etihad Airways both into and out of the stop
$35 more than the cheapest fare without a long stop on the same dates
found 19 hours ago
Tashkent · return
$854
20 h in Abu Dhabi (AUH) on the way back · overnight connection
8 Nov – 23 Nov · ORD → TAS · Etihad Airways
out 1 stop, back 1 stop · Etihad Airways both into and out of the stop
$69 less than the cheapest fare without a long stop on the same dates
found yesterday
Stop in Munich
2 trips go through Munich. The best are here.
Moscow · one-way
$845
9 h 20 min in Munich (MUC) on the way there · connection may need a visa
23 Jul 2027 · ORD → VKO · Lufthansa
2 stops · Lufthansa both into and out of the stop
$79 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Bishkek · return
$1,702
22 h 10 min in Munich (MUC) on the way back · overnight connection
16 Nov – 15 Dec · ORD → BSZ · Turkish Airlines
out 1 stop, back 3 stops · in with Turkish Airlines, out with Aer Lingus
$276 more than the cheapest fare without a long stop on the same dates
found 5 days ago
Stop in Baku
2 trips go through Baku. The best are here.
Moscow · one-way
$1,190
10 h 45 min in Baku (GYD) on the way there
23 Jul 2027 · ORD → DME · Turkish Airlines
2 stops · in with Turkish Airlines, out with Azerbaijan Airlines
$424 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Bishkek · return
$1,288
19 h 15 min in Baku (GYD) on the way there · overnight connection
29 Nov – 6 Dec · ORD → BSZ · Turkish Airlines
out 2 stops, back 2 stops · Azerbaijan Airlines both into and out of the stop
$1,095 less than the cheapest fare without a long stop on this route (29 Nov – 5 Dec)
found 3 days ago
Stop in Belgrade
2 trips go through Belgrade. The best are here.
Moscow · return
$2,482
19 h 10 min in Belgrade (BEG) on the way back · overnight connection
25 Dec – 30 Dec · ORD → VKO · Air Serbia
out 1 stop, back 1 stop · Air Serbia both into and out of the stop
$634 more than the cheapest fare without a long stop on the same dates
found yesterday
Istanbul · return
$1,528
12 h 30 min in Belgrade (BEG) on the way there
26 Dec – 10 Jan 2027 · ORD → IST · Turkish Airlines
out 1 stop, back nonstop · Air Serbia both into and out of the stop
$134 more than the cheapest fare without a long stop on the same dates
found 2 days ago
Stop in Baltimore
1 trip goes through Baltimore.
Fort Lauderdale · return
$186
20 h 2 min in Baltimore (BWI) on the way there · overnight connection
11 Dec – 21 Dec · ORD → FLL · Frontier Airlines
out 1 stop, back nonstop · Frontier Airlines both into and out of the stop
$44 less than the cheapest fare without a long stop on the same dates
found yesterday
Stop in Cape Girardeau
1 trip goes through Cape Girardeau.
Orlando · one-way
$349
20 h 50 min in Cape Girardeau (CGI) on the way there · overnight connection
12 Jan 2027 · ORD → SFB · Contour Airlines
1 stop · Contour Airlines both into and out of the stop
$274 more than the cheapest fare without a long stop on the same dates
found yesterday
Stop in Frankfurt
1 trip goes through Frankfurt.
Istanbul · one-way
$399
8 h in Frankfurt (FRA) on the way there · connection may need a visa
27 Jan 2027 · ORD → IST · United Airlines
1 stop · in with United Airlines, out with Lufthansa
$122 less than the cheapest fare without a long stop on the same dates
found 3 days ago
Stop in Las Vegas
1 trip goes through Las Vegas.
Los Angeles · return
$430
23 h 38 min in Las Vegas (LAS) on the way back · overnight connection
20 Nov – 1 Dec · ORD → LAX · Frontier Airlines
out 1 stop, back 1 stop · Frontier Airlines both into and out of the stop
$177 more than the cheapest fare without a long stop on this route (30 Nov – 15 Dec)
found 14 hours ago
Stop in Copenhagen
1 trip goes through Copenhagen.
Istanbul · one-way
$492
19 h 30 min in Copenhagen (CPH) on the way there · overnight connection
8 Nov · ORD → SAW · Icelandair
2 stops · in with Icelandair, out with Pegasus Airlines
$115 more than the cheapest fare without a long stop on the same dates
found 4 days ago
Stop in Madrid
2 trips go through Madrid. The best are here.
Bishkek · return
$1,132
23 h 25 min in Madrid (MAD) on the way back · overnight connection
11 Jan 2027 – 12 Mar 2027 · ORD → BSZ · Air Canada
out 3 stops, back 3 stops · in with Pegasus Airlines, out with Air Canada
$1,251 less than the cheapest fare without a long stop on this route (29 Nov – 5 Dec)
found 3 days ago
Istanbul · return
$918
20 h in Madrid (MAD) on the way back · overnight connection · connection may need a visa
26 Oct – 6 Nov · ORD → SAW · TAP Air Portugal
out 2 stops, back 2 stops · in with Pegasus Airlines, out with TAP Air Portugal
$18 less than the cheapest fare without a long stop on the same dates
found 6 days ago
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