
Cheap Holidays to Old Town Chicago
- Top deals for trips to Old Town Chicago
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Old Town Chicago
Price found within the past 48 hours. Click for updated prices.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Art Villa
West Town
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
During your stay at Art Villa , you'll be within walking distance of United Center. Features include free WiFi in public areas, free self-parking and a free round-trip airport shuttle. Built in 2017, this luxury aparthotel has 5 apartments. Some of the pet-friendly amenities that this property offers include food and water bowls and an off-lead area. Each apartment offers free WiFi and rooftop hot tubs.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Arlo Chicago
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
The sightseeing around Arlo Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym.
Old Town Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Art Villa
West Town
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
During your stay at Art Villa , you'll be within walking distance of United Center. Features include free WiFi in public areas, free self-parking and a free round-trip airport shuttle. Built in 2017, this luxury aparthotel has 5 apartments. Some of the pet-friendly amenities that this property offers include food and water bowls and an off-lead area. Each apartment offers free WiFi and rooftop hot tubs.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Arlo Chicago
Downtown Chicago
15 Sept - 21 Sept
6 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 6 hours ago
The sightseeing around Arlo Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym.
Best Old Town Chicago hotel deals for your holiday

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
The price is €254 per night
€254
7 Jul - 8 Jul
includes taxes & fees
2.6 km from Old Town Chicago
Our customers tell us they can't get enough of InterContinental Chicago Magnificent Mile by IHG's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and an indoor pool.
Uima-allas
Kylpylä

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €143 per night
€143
4 Aug - 5 Aug
includes taxes & fees
4.22 km from Old Town Chicago
Our customers tell us they can't get enough of Congress Plaza Hotel's great location. During your stay, you're just a quick walk from Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Ilmainen Wi-Fi
Ravintola

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €168 per night
€168
10 Jul - 11 Jul
includes taxes & fees
1.95 km from Old Town Chicago
The shopping around Hilton Chicago/Magnificent Mile Suites gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas, plus a gym and a business centre.

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
The price is €214 per night
€214
27 Jul - 28 Jul
includes taxes & fees
23.07 km from Old Town Chicago
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Rosemont Theatre. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.
Ilmaiset lentokenttäkuljetukset
Lemmikkiystävällinen

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €192 per night
€192
10 Jul - 11 Jul
includes taxes & fees
2.28 km from Old Town Chicago
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
Uima-allas
Aamiainen sisältyy hintaan

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €158 per night
€158
7 Jul - 8 Jul
includes taxes & fees
2.98 km from Old Town Chicago
The sightseeing around citizenM Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a gym are available.
Ilmainen Wi-Fi
Ravintola
Don't see what you're looking for?
See all available properties in Old Town Chicago
View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cheap flights to Old Town Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
MDW
Chicago
€218 Return, found 3 hours ago
€218
Return
found 3 hours ago
LAX
Los Angeles
ORD
Chicago
€218 Return, found 3 hours ago
€218
Return
found 3 hours ago
LAX
Los Angeles
ORD
Chicago
€233 Return, found 3 hours ago
€233
Return
found 3 hours ago
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^Savings based on all package bookings with Flight + Hotel made on ebookers.fi from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.