Far Southeast Side Cheap Vacations
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Flight and Cheap hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $2,073, price is now CA $1,314 per person
CA $1,314
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $3,565, price is now CA $1,963 per person
CA $1,963
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
The hotel has no parking and you will have to pay $70.00 per day if you self park and if you use valet parking it would be $90.00 per day. For the price they should provide complementary breakfast as I have paid less for better quality places which include breakfast and parking.
Reviewed on May 25, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,745, price is now CA $1,673 per person
CA $1,673
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,726, price is now CA $1,735 per person
CA $1,735
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Beautiful views and amazing amenities
Reviewed on May 25, 2026
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Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
Price was CA $1,829, price is now CA $1,425 per person
CA $1,425
per person
Jun 30 - Jul 3
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Fantastic hotel and amazing spa! Beautiful room with fantastic staff
Reviewed on May 16, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,806, price is now CA $2,598 per person
CA $2,598
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $4,611, price is now CA $3,629 per person
CA $3,629
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
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Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,405, price is now CA $950 per person
CA $950
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,709, price is now CA $1,707 per person
CA $1,707
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Beautiful views and amazing amenities
Reviewed on May 25, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,833, price is now CA $1,169 per person
CA $1,169
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
The hotel has no parking and you will have to pay $70.00 per day if you self park and if you use valet parking it would be $90.00 per day. For the price they should provide complementary breakfast as I have paid less for better quality places which include breakfast and parking.
Reviewed on May 25, 2026
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View all trips4 Night Cheap holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,630, price is now CA $1,010 per person
CA $1,010
per person
Jul 16 - Jul 20
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
The hotel has no parking and you will have to pay $70.00 per day if you self park and if you use valet parking it would be $90.00 per day. For the price they should provide complementary breakfast as I have paid less for better quality places which include breakfast and parking.
Reviewed on May 25, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,915, price is now CA $1,240 per person
CA $1,240
per person
Aug 11 - Aug 15
found 4 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,709, price is now CA $1,138 per person
CA $1,138
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Beautiful views and amazing amenities
Reviewed on May 25, 2026
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