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Search results; Over 1,000 homes

Top guest favourite
Flat in Near North Side
Luxury Loft Collection COMBO 01/03 | Terrace
2-min walk
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
Superhost
Flat in Near North Side
Luxury Loft Collection 01 - Terrace - River North
2-min walk
23–28 Aug
4.9 out of 5 average rating, 121 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3-min walk
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Flat in Near North Side
Luxury Loft Collection 1, 2, 3
2-min walk
29 Oct – 3 Nov
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Near North Side
Gold Coast Luxury: 2BR with Sweeping City Vistas
5-min walk
26–31 Aug
4.93 out of 5 average rating, 120 reviews
Flat in Chicago
Gold Coast Gem
3-min walk
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Near North Side
Kasa | Elevate your stay, Premium Studio | Chicago
4-min walk
19–24 Jul
4.73 out of 5 average rating, 64 reviews
Hotel in Chicago
Deluxe two bedroom suite
10-min walk
9–14 Aug
Top guest favourite
Home in Near North Side
Private Downtown Retreat with Rooftop Oasis
5-min walk
15–20 Aug
4.98 out of 5 average rating, 115 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
20-min drive
22–27 Jul
4.97 out of 5 average rating, 93 reviews
Guest favourite
Flat in Chicago
Downtown Penthouse Huge Patio with Great View
20-min drive
9–14 Aug
4.99 out of 5 average rating, 74 reviews
Home in Chicago
Historic & Perfectly Modern, 5 Beds/2 Bath/Parking
20-min drive
16–21 Aug
New place to stay
Guest favourite
Flat in Lower West Side
Pilsen Modern Chic Retreat
30-min drive
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
20-min drive
14–19 Jul
4.98 out of 5 average rating, 40 reviews
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
9-min walk
16–21 Aug
New place to stay
Superhost
Flat in Chicago
Luxury Penthouse COMBO 07/02 Terrace | River North
3-min walk
17–22 Sept
Guest favourite
Flat in Near North Side
Kasa | Walk Magnificent Mile | River North
5-min walk
13–18 Sept
4.84 out of 5 average rating, 202 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
30-min drive
2–7 Aug
5.0 out of 5 average rating, 13 reviews