Discover hotels near Chicago for weekend escapes

  1. Health & safety New safety measures are in place at this hotel. Read more here

    Vermont, United States

    Twin Farms

    Style

    All-star art barn

    Setting

    Verdant Vermont countryside

    Price per night from (ex tax)$2,000.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    $100 spa treatment credit
  2. Health & safety New safety measures are in place at this hotel. Read more here

    Toronto, Canada

    The Hazelton Hotel

    Style

    Glossy grey, fully glam

    Setting

    Well-to-do Yorkville

    Price per night from (ex tax)$404.70

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A $50 spa credit to spend on treatments
  3. Health & safety New safety measures are in place at this hotel. Read more here

    Boston, United States

    XV Beacon

    Style

    Stately city stay

    Setting

    Beside beautiful Boston Common

    Price per night from (ex tax)$395.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    Daily Continental breakfast for two ($40 value)
  4. Health & safety New safety measures are in place at this hotel. Read more here

    New Orleans, United States

    Maison de la Luz

    Style

    The light fantastic

    Setting

    Edge of the Warehouse District

    Price per night from (ex tax)$269.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    Two welcome cocktails at Bar Marilou
  5. New Orleans, United States

    Soniat House

    Style

    Colonial-Creole townhouse

    Setting

    Vivacious Vieux Carré

    Price per night from (ex tax)$245.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A copy of La Bouche Creole cookbook by Leon Soniat, and SilverSmith and GoldSmith members receive a free welcome glass of champagne
  6. Health & safety New safety measures are in place at this hotel. Read more here

    Boston, United States

    The Whitney Hotel

    Style

    Red-brick revival

    Setting

    Beaming Beacon

    Price per night from (ex tax)$225.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A full American breakfast for two in Peregrine; GoldSmiths also get a bottle of wine
  7. Health & safety New safety measures are in place at this hotel. Read more here

    New Orleans, United States

    The Old No 77 Hotel & Chandlery

    Style

    Bedknobs and candlesticks

    Setting

    Bustling Big Easy

    Price per night from (ex tax)$217.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    Tout La token for one coffee or tea a day, for each guest, from the hotel's coffee bar
  8. Health & safety New safety measures are in place at this hotel. Read more here

    Washington, DC, United States

    Line DC

    Style

    Take me to church

    Setting

    Arty Adams Morgan

    Price per night from (ex tax)$199.00

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A welcome bouquet of blooms from the Little Shop of Flowers
  9. Toronto, Canada

    The Drake

    Style

    Cool, cultural cutting-edge

    Setting

    Art and Design District of Parkdale

    Price per night from (ex tax)$171.91

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A bottle of Starving Artist house red or white wine in your room on arrival
  10. Montreal, Canada

    Hôtel William Gray

    Style

    Merchant’s maison, à la mode

    Setting

    Very Vieux-Montréal

    Price per night from (ex tax)$165.90

    Why book with us?

    Best-price guarantee

    Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

    Free Smith Extras on arrival

    From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

    Here for you 24/7

    Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

    Anonymously reviewed

    Every hotel is reviewed by undercover tastemakers (and their partners)

    Smith Extra

    A CAD25 spa credit a room, for each stay