Cheap Flights from Halifax to Chicago
Browse current best options from Halifax. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Halifax
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Halifax to Chicago
Explore current cheapest deals departing from Halifax to Chicago
Round trip
Sort by: Cheapest
October 7 - October 14
YHZ - Chicago
$399
$324
Round trip
September 15 - September 20
YHZ - Chicago
$367
$328
Round trip
August 19 - August 25
YHZ - Chicago
$471
$329
Round trip
October 11 - October 15
YHZ - Chicago
$408
$329
Round trip
September 12 - September 19
YHZ - Chicago
$361
$330
Round trip
October 10 - October 14
YHZ - Chicago
$407
$332
Round trip
September 15 - September 22
YHZ - Chicago
$361
$334
Round trip
December 9 - December 16
YHZ - Chicago
$495
$337
Round trip
December 9 - December 22
YHZ - Chicago
$484
$337
Round trip
December 15 - December 16
YHZ - Chicago
$499
$337
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Halifax to Chicago
How much is a round trip from Halifax to Chicago
Regular price: $327 - $720
Prices are currently below the regular range for flights from Halifax to Chicago.
The regular price range for flights from Halifax to Chicago is between $327 and $720. The current lowest deal is $324 with Porter Airlines for travel from Oct 7-Oct 14.
now $324
Low $327
High $720
The cheapest time to fly from Halifax to Chicago
The cheapest month to fly from YHZ to CHI is April, with a median price of $358. The most expensive month is December, with a median price of $971. Prices are generally lower from January to October.
April
Flights from $358
December
Flights from $971
Direct flights from Halifax to Chicago
United Airlines
Last-minute flights going from Halifax to Chicago
Sun, Jun 21
YHZ - Chicago
Halifax (YHZ) - Chicago (ORD)
Deutsche Luft Hansa
$508
$500
One-way
Fri, Jun 26
YHZ - Chicago
Halifax (YHZ) - Chicago (MDW)
Porter Airlines
$540
$489
One-way
Mon, Jun 29
YHZ - Chicago
Halifax (YHZ) - Chicago (ORD)
$419
$380
One-way
Tue, Jun 30
YHZ - Chicago
Halifax (YHZ) - Chicago (ORD)
$442
$380
One-way
Tue, Jun 30
YHZ - Chicago
Halifax (YHZ) - Chicago (ORD)
$410
$418
One-way
Wed, Jul 1
YHZ - Chicago
Halifax (YHZ) - Chicago (MDW)
Porter Airlines
$433
$355
One-way
Biggest price drops on these dates for flights from Halifax to Chicago
Dec 15 - Dec 16
$499 → $337
32%
Dec 15 - Dec 22
$497 → $337
32%
Dec 9 - Dec 16
$495 → $337
32%
Dec 9 - Dec 22
$484 → $337
30%
Popular Airports to fly from Halifax to Chicago
Halifax - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Halifax to Chicago are below the typical level, with deals around $324.
📅 Best time to fly
April is historically the cheapest month
Historically, April is the cheapest month to fly from Halifax to Chicago, with a median price of $358.
⏱️ Flight duration
Connecting flights take 12h 10m
The median flight time for connecting flights from Halifax to Chicago is 12 hours 10 minutes.
✈️ Airlines & availability
Connecting flights are dominant on this route
Connecting flights are dominant on this route, making up 96.5% of all deals.
🏆 Airline highlight
Porter Airlines offers deals from $324
Porter Airlines recently offered a deal from Halifax to Chicago for $324.
🎯 Booking tip
Deals appear frequently (1 per day)
Deals from Halifax to Chicago appear frequently, with about 1 deal per day historically.
Halifax main airports to depart from
Halifax Stanfield International (YHZ)
Halifax Stanfield International is a good option for flights from Halifax to Chicago.
📍 ~30 km from city center (reachable by car)
💸 Flights from ~$324
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub, offering extensive connections for your arrival in Chicago.
📍 ~20 km from Chicago city center (reachable by car or public transport).
💸 Flights from ~$324
Chicago Midway International (MDW)
Chicago Midway International Airport offers a convenient arrival option for flights to Chicago from Halifax.
📍 ~15 km from Chicago city center (reachable by car or public transport).
💸 Flights from ~$329
Chicago Rockford International (RFD)
Chicago Rockford International Airport provides an alternative arrival point for your trip to the Chicago area.
📍 ~120 km from Chicago city center (reachable by car).
💸 Flights from ~$383
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International Airport (MKE) is an excellent alternative for Chicago travelers, despite potential traffic on I-94.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$402
South Bend International (SBN)
South Bend International Airport (SBN) is a close alternative to Chicago, offering easier security and parking.
📍 ~125 km from Chicago (reachable by rail)
💸 Flights from ~$431
Gerald R. Ford International (GRR)
Gerald R. Ford International Airport (GRR) is a major regional hub for travelers on the eastern side of Chicago.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$332
Dane County Regional (MSN)
Dane County Regional Airport (MSN) is a reliable and less congested option, though it is a secondary choice to MKE.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$439
Fort Wayne International (FWA)
Fort Wayne International Airport (FWA) is an alternative for travelers in the southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$446
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Halifax to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From YHZ
Elite
Aug 04
Chicago, United States
87% AI deal score
$1,833
$826
Save $1,007
From YHZ
Elite
Aug 09
Chicago, United States
87% AI deal score
$1,481
$707
Save $774
From YHZ
Elite
Aug 09
Chicago, United States
87% AI deal score
$1,515
$707
Save $808
From YHZ
Elite
Aug 10
Chicago, United States
87% AI deal score
$1,495
$707
Save $788
From YHZ
Elite
Aug 10
Chicago, United States
87% AI deal score
$1,520
$707
Save $813
From YHZ
Elite
Jul 28
Chicago, United States
87% AI deal score
$1,396
$707
Save $689
From YHZ
Elite
Aug 12
Chicago, United States
87% AI deal score
$1,516
$720
Save $796
From YHZ
Elite
Jul 27
Chicago, United States
87% AI deal score
$1,400
$720
Save $680
From YHZ
Elite
Jul 15
Chicago, United States
87% AI deal score
$1,405
$720
Save $685
From YHZ
Elite
Jul 31
Chicago, United States
87% AI deal score
$1,395
$720
Save $675
From YHZ
Elite
Jul 17
Chicago, United States
87% AI deal score
$1,396
$720
Save $676
From YHZ
Elite
Aug 13
Chicago, United States
87% AI deal score
$1,520
$720
Save $800
From YHZ
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,734
$826
Save $908
From YHZ
Elite
Aug 23
Chicago, United States
86% AI deal score
$1,754
$833
Save $921
From YHZ
Elite
Aug 11
Chicago, United States
86% AI deal score
$1,515
$554
Save $961
From YHZ
Elite
Jul 29
Chicago, United States
86% AI deal score
$1,399
$559
Save $840
From YHZ
Elite
Jul 29
Chicago, United States
86% AI deal score
$1,392
$559
Save $833
From YHZ
Elite
Aug 02
Chicago, United States
86% AI deal score
$1,457
$707
Save $750
From YHZ
Elite
Aug 04
Chicago, United States
86% AI deal score
$1,457
$707
Save $750
From YHZ
Elite
Aug 02
Chicago, United States
86% AI deal score
$1,457
$707
Save $750
From YHZ
Elite
Aug 04
Chicago, United States
86% AI deal score
$1,450
$707
Save $743
From YHZ
Elite
Aug 05
Chicago, United States
86% AI deal score
$1,459
$720
Save $739
From YHZ
Elite
Aug 06
Chicago, United States
86% AI deal score
$1,459
$720
Save $739
From YHZ
Elite
Aug 16
Chicago, United States
86% AI deal score
$1,485
$722
Save $763
From YHZ
Elite
Jun 30
Chicago, United States
85% AI deal score
$1,686
$862
Save $824
From YHZ
Elite
Aug 03
Chicago, United States
85% AI deal score
$1,456
$559
Save $897
From YHZ
Elite
Aug 03
Chicago, United States
85% AI deal score
$1,456
$559
Save $897
From YHZ
Elite
Jun 29
Chicago, United States
85% AI deal score
$1,419
$604
Save $815
From YHZ
Elite
Jun 29
Chicago, United States
85% AI deal score
$1,424
$604
Save $820
From YHZ
Elite
Jul 27
Chicago, United States
85% AI deal score
$1,408
$604
Save $804
From YHZ
Elite
Jun 28
Chicago, United States
85% AI deal score
$1,432
$610
Save $822
From YHZ
Elite
Jun 25
Chicago, United States
85% AI deal score
$1,434
$610
Save $824
From YHZ
Elite
Jul 13
Chicago, United States
84% AI deal score
$1,398
$610
Save $788
From YHZ
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,383
$610
Save $773
From YHZ
Elite
Jul 15
Chicago, United States
84% AI deal score
$1,392
$610
Save $782
From YHZ
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,396
$610
Save $786
From YHZ
Elite
Jul 15
Chicago, United States
84% AI deal score
$1,400
$610
Save $790
From YHZ
Elite
Jul 13
Chicago, United States
84% AI deal score
$1,402
$610
Save $792
From YHZ
Elite
Jul 27
Chicago, United States
84% AI deal score
$1,400
$622
Save $778
From YHZ
Elite
Jul 27
Chicago, United States
84% AI deal score
$1,403
$622
Save $781
From YHZ
Elite
Jul 15
Chicago, United States
84% AI deal score
$1,397
$628
Save $769
From YHZ
Elite
Jul 15
Chicago, United States
84% AI deal score
$1,397
$628
Save $769
From YHZ
Elite
Aug 12
Chicago, United States
84% AI deal score
$1,520
$628
Save $892
From YHZ
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,396
$628
Save $768
From YHZ
Elite
Jul 31
Chicago, United States
84% AI deal score
$1,391
$628
Save $763
From YHZ
Elite
Jul 31
Chicago, United States
84% AI deal score
$1,392
$628
Save $764
From YHZ
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,396
$628
Save $768
From YHZ
Elite
Jul 13
Chicago, United States
84% AI deal score
$1,397
$628
Save $769
From YHZ
Elite
Jun 26
Chicago, United States
84% AI deal score
$1,429
$636
Save $793
From YHZ
Elite
Jul 20
Chicago, United States
84% AI deal score
$1,408
$636
Save $772
From YHZ
Elite
Jul 20
Chicago, United States
84% AI deal score
$1,396
$636
Save $760
From YHZ
Elite
Jul 18
Chicago, United States
83% AI deal score
$1,298
$792
Save $506
From YHZ
Elite
Aug 05
Chicago, United States
83% AI deal score
$1,452
$628
Save $824
From YHZ
Elite
Aug 05
Chicago, United States
83% AI deal score
$1,459
$628
Save $831
From YHZ
Elite
Aug 06
Chicago, United States
83% AI deal score
$1,452
$628
Save $824
From YHZ
Elite
Aug 06
Chicago, United States
83% AI deal score
$1,465
$628
Save $837
From YHZ
Elite
Aug 11
Chicago, United States
83% AI deal score
$1,495
$646
Save $849
From YHZ
Elite
Jul 29
Chicago, United States
83% AI deal score
$1,398
$651
Save $747
From YHZ
Elite
Jul 20
Chicago, United States
83% AI deal score
$1,398
$654
Save $744
From YHZ
Elite
Jul 20
Chicago, United States
83% AI deal score
$1,396
$654
Save $742
From YHZ
Elite
Aug 04
Chicago, United States
82% AI deal score
$1,816
$778
Save $1,038
From YHZ
Elite
Aug 03
Chicago, United States
82% AI deal score
$1,456
$651
Save $805
From YHZ
Elite
Jul 28
Chicago, United States
82% AI deal score
$1,411
$689
Save $722
From YHZ
Elite
Jul 28
Chicago, United States
82% AI deal score
$1,398
$707
Save $691
From YHZ
Elite
Jul 17
Chicago, United States
81% AI deal score
$1,298
$867
Save $431
From YHZ
Elite
Aug 01
Chicago, United States
81% AI deal score
$1,367
$911
Save $456
From YHZ
Elite
Jun 30
Chicago, United States
80% AI deal score
$1,341
$962
Save $379
From YHZ
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,298
$927
Save $371
From YHZ
Elite
Jul 21
Chicago, United States
79% AI deal score
$1,414
$1,050
Save $364
From YHZ
Elite
Jun 23
Chicago, United States
73% AI deal score
$1,277
$943
Save $334
From YHZ
Elite
Jun 25
Chicago, United States
73% AI deal score
$1,371
$1,014
Save $357
From YHZ
Elite
Jul 15
Chicago, United States
72% AI deal score
$1,260
$1,015
Save $245
From YHZ
Elite
Aug 01
Chicago, United States
71% AI deal score
$1,397
$1,163
Save $234
From YHZ
Elite
Jul 21
Chicago, United States
71% AI deal score
$1,396
$1,159
Save $237
From YHZ
Elite
Jul 15
Chicago, United States
70% AI deal score
$1,794
$1,489
Save $305
From YHZ
Elite
Jul 15
Chicago, United States
69% AI deal score
$1,255
$1,142
Save $113
From YHZ
Elite
Jul 17
Chicago, United States
67% AI deal score
$1,298
$1,265
Save $33
From YHZ
Elite
Aug 23
Chicago, United States
67% AI deal score
$1,381
$1,342
Save $39
From YHZ
Elite
Aug 04
Chicago, United States
67% AI deal score
$1,499
$1,475
Save $24
From YHZ
Elite
Jul 14
Chicago, United States
65% AI deal score
$1,869
From YHZ
Elite
Jul 12
Chicago, United States
65% AI deal score
$1,869
From YHZ
Elite
Jul 20
Chicago, United States
50% AI deal score
$1,929
From YHZ
Elite
Jul 16
Chicago, United States
50% AI deal score
$2,018
From YHZ
Elite
Jul 28
Chicago, United States
50% AI deal score
$2,019
From YHZ
Elite
Jul 30
Chicago, United States
50% AI deal score
$2,019
From YHZ
Elite
Jul 17
Chicago, United States
50% AI deal score
$2,019
From YHZ
Elite
Jul 21
Chicago, United States
49% AI deal score
$2,322
From YHZ
Elite
Aug 02
Chicago, United States
48% AI deal score
$1,316
From YHZ
Elite
Jul 17
Chicago, United States
45% AI deal score
$1,257
From YHZ
Elite
Jul 11
Chicago, United States
45% AI deal score
$1,280
From YHZ
Elite
Jul 13
Chicago, United States
45% AI deal score
$1,287
From YHZ
Elite
Jun 30
Chicago, United States
43% AI deal score
$1,784
From YHZ
Elite
Aug 07
Chicago, United States
42% AI deal score
$1,759
From YHZ
Elite
Jul 16
Chicago, United States
40% AI deal score
$1,868
From YHZ
Elite
Jul 06
Chicago, United States
40% AI deal score
$2,276