Holidays to Chicago - Cheap Flights and Hotels in Chicago

Holidays to Chicago

Set on the shores of Lake Michigan and with some amazing modern architecture, Chicago is a city that’s full of surprises. Listen to live blues and jazz, visit the elegant shops on the ‘Magnificent Mile’, or explore the lakefront parks and beaches. First class shops, beautiful parks and a varied art and music scene make this an ideal place for a break. The view from the Sears Tower is quite breathtaking giving a fabulous overview of the city.

Hotel 71

3 stars

0.6 miles South from the centre of Chicago map

Reviewer score 4.1 / 5 213 reviews
Special Promotion
£923.10 average per person
Total £1,846.19
£923.10 average per person
Total £1,846.19
£923.10 average per person
Total £1,846.19
£923.10 average per person
Total £1,846.19
£961.60 average per person
Total £1,923.19
£973.10 average per person
Total £1,946.19
£973.10 average per person
Total £1,946.19
£976.29 average per person
Total £1,952.57
£976.72 average per person
Total £1,953.43
£996.10 average per person
Total £1,992.19

Hotel Lincoln a Joie de Vivre Hotel

4 stars

1.4 miles North from the centre of Chicago map

Not yet reviewed – Be the first to review this hotel
Special Promotion
£885.46 average per person
Total £1,770.92
£885.46 average per person
Total £1,770.92
£885.46 average per person
Total £1,770.92
£885.46 average per person
Total £1,770.92
£923.96 average per person
Total £1,847.92
£935.46 average per person
Total £1,870.92
£935.46 average per person
Total £1,870.92
£938.65 average per person
Total £1,877.30
£939.08 average per person
Total £1,878.16
£958.46 average per person
Total £1,916.92

Omni Chicago Hotel

4 stars

0.1 miles Southeast from the centre of Chicago map

Reviewer score 4.4 / 5 120 reviews
£927.14 average per person
Total £1,854.28
£927.14 average per person
Total £1,854.28
£927.14 average per person
Total £1,854.28
£927.14 average per person
Total £1,854.28
£965.64 average per person
Total £1,931.28
£977.14 average per person
Total £1,954.28
£977.14 average per person
Total £1,954.28
£980.33 average per person
Total £1,960.66
£980.76 average per person
Total £1,961.52
£1,000.14 average per person
Total £2,000.28

The Whitehall Hotel

4 stars

0.2 miles North from the centre of Chicago map

Reviewer score 3.8 / 5 961 reviews
Special Promotion
£845.54 average per person
Total £1,691.07
£845.54 average per person
Total £1,691.07
£845.54 average per person
Total £1,691.07
£845.54 average per person
Total £1,691.07
£884.04 average per person
Total £1,768.07
£895.54 average per person
Total £1,791.07
£895.54 average per person
Total £1,791.07
£898.73 average per person
Total £1,797.45
£899.16 average per person
Total £1,798.31
£918.54 average per person
Total £1,837.07

MileNorth, A Chicago Hotel

4 stars

0.1 miles East from the centre of Chicago map

Reviewer score 4.4 / 5 223 reviews
Special Promotion
£978.22 average per person
Total £1,956.43
£978.22 average per person
Total £1,956.43
£978.22 average per person
Total £1,956.43
£978.22 average per person
Total £1,956.43
£1,016.72 average per person
Total £2,033.43
£1,028.22 average per person
Total £2,056.43
£1,028.22 average per person
Total £2,056.43
£1,031.41 average per person
Total £2,062.81
£1,031.84 average per person
Total £2,063.67
£1,051.22 average per person
Total £2,102.43

Congress Plaza Hotel at Grant Park

3 stars

1.4 miles South from the centre of Chicago map

Reviewer score 3.4 / 5 637 reviews
Special Promotion
£810.61 average per person
Total £1,621.21
£810.61 average per person
Total £1,621.21
£810.61 average per person
Total £1,621.21
£810.61 average per person
Total £1,621.21
£849.11 average per person
Total £1,698.21
£860.61 average per person
Total £1,721.21
£860.61 average per person
Total £1,721.21
£863.80 average per person
Total £1,727.59
£864.23 average per person
Total £1,728.45
£883.61 average per person
Total £1,767.21

Chicago O'Hare Garden Hotel

2 stars

12.0 miles Northwest from the centre of Chicago map

Reviewer score 2.6 / 5 337 reviews
Special Promotion
  • Save 50% off your stay

View all available promotions

£730.42 average per person
Total £1,460.83
£730.42 average per person
Total £1,460.83
£730.42 average per person
Total £1,460.83
£730.42 average per person
Total £1,460.83
£768.92 average per person
Total £1,537.83
£780.42 average per person
Total £1,560.83
£780.42 average per person
Total £1,560.83
£783.61 average per person
Total £1,567.21
£784.04 average per person
Total £1,568.07
£803.42 average per person
Total £1,606.83
1 room left!

Raffaello Hotel

4 stars

0.3 miles Northeast from the centre of Chicago map

Reviewer score 4 / 5 93 reviews
Special Promotion
£914.83 average per person
Total £1,829.66
£914.83 average per person
Total £1,829.66
£914.83 average per person
Total £1,829.66
£914.83 average per person
Total £1,829.66
£953.33 average per person
Total £1,906.66
£964.83 average per person
Total £1,929.66
£964.83 average per person
Total £1,929.66
£968.02 average per person
Total £1,936.04
£968.45 average per person
Total £1,936.90
£987.83 average per person
Total £1,975.66

Amalfi Hotel Chicago

4 stars

0.5 miles Southwest from the centre of Chicago map

Reviewer score 4.4 / 5 604 reviews
£923.46 average per person
Total £1,846.91
£923.46 average per person
Total £1,846.91
£923.46 average per person
Total £1,846.91
£923.46 average per person
Total £1,846.91
£961.96 average per person
Total £1,923.91
£973.46 average per person
Total £1,946.91
£973.46 average per person
Total £1,946.91
£976.65 average per person
Total £1,953.29
£977.08 average per person
Total £1,954.15
£996.46 average per person
Total £1,992.91

The Allerton Hotel Chicago, Magnificent Mile

4 stars

0.1 miles Southeast from the centre of Chicago map

Reviewer score 4 / 5 423 reviews
Special Promotion
  • Non-Refundable Special

View all available promotions

£904.22 average per person
Total £1,808.44
£904.22 average per person
Total £1,808.44
£904.22 average per person
Total £1,808.44
£904.22 average per person
Total £1,808.44
£942.72 average per person
Total £1,885.44
£954.22 average per person
Total £1,908.44
£954.22 average per person
Total £1,908.44
£957.41 average per person
Total £1,914.82
£957.84 average per person
Total £1,915.68
£977.22 average per person
Total £1,954.44
1 room left!

The James Hotel Chicago

4 stars

0.3 miles Southwest from the centre of Chicago map

Reviewer score 4.5 / 5 103 reviews
£974.84 average per person
Total £1,949.68
£974.84 average per person
Total £1,949.68
£974.84 average per person
Total £1,949.68
£974.84 average per person
Total £1,949.68
£1,013.34 average per person
Total £2,026.68
£1,024.84 average per person
Total £2,049.68
£1,024.84 average per person
Total £2,049.68
£1,028.03 average per person
Total £2,056.06
£1,028.46 average per person
Total £2,056.92
£1,047.84 average per person
Total £2,095.68

The Talbott Hotel

4 stars

0.3 miles Northwest from the centre of Chicago map

Reviewer score 4.6 / 5 462 reviews
£990.99 average per person
Total £1,981.98
£990.99 average per person
Total £1,981.98
£990.99 average per person
Total £1,981.98
£990.99 average per person
Total £1,981.98
£1,029.49 average per person
Total £2,058.98
£1,040.99 average per person
Total £2,081.98
£1,040.99 average per person
Total £2,081.98
£1,044.18 average per person
Total £2,088.36
£1,044.61 average per person
Total £2,089.22
£1,063.99 average per person
Total £2,127.98

PUBLIC Chicago

4 stars

0.7 miles North from the centre of Chicago map

Reviewer score 3.4 / 5 5 reviews
£949.36 average per person
Total £1,898.72
£949.36 average per person
Total £1,898.72
£949.36 average per person
Total £1,898.72
£949.36 average per person
Total £1,898.72
£987.86 average per person
Total £1,975.72
£999.36 average per person
Total £1,998.72
£999.36 average per person
Total £1,998.72
£1,002.55 average per person
Total £2,005.10
£1,002.98 average per person
Total £2,005.96
£1,022.36 average per person
Total £2,044.72

Wyndham Blake Chicago

4 stars

1.5 miles South from the centre of Chicago map

Reviewer score 4 / 5 224 reviews
£893.89 average per person
Total £1,787.78
£893.89 average per person
Total £1,787.78
£893.89 average per person
Total £1,787.78
£893.89 average per person
Total £1,787.78
£932.39 average per person
Total £1,864.78
£943.89 average per person
Total £1,887.78
£943.89 average per person
Total £1,887.78
£947.08 average per person
Total £1,894.16
£947.51 average per person
Total £1,895.02
£966.89 average per person
Total £1,933.78

The Sutton Place Hotel -- Chicago

4 stars

0.4 miles North from the centre of Chicago map

Reviewer score 4.5 / 5 132 reviews
£987.33 average per person
Total £1,974.66
£987.33 average per person
Total £1,974.66
£987.33 average per person
Total £1,974.66
£987.33 average per person
Total £1,974.66
£1,025.83 average per person
Total £2,051.66
£1,037.33 average per person
Total £2,074.66
£1,037.33 average per person
Total £2,074.66
£1,040.52 average per person
Total £2,081.04
£1,040.95 average per person
Total £2,081.90
£1,060.33 average per person
Total £2,120.66

Palomar Chicago, a Kimpton Hotel

4 stars

0.4 miles Southwest from the centre of Chicago map

Reviewer score 4.2 / 5 27 reviews
£978.94 average per person
Total £1,957.88
£978.94 average per person
Total £1,957.88
£978.94 average per person
Total £1,957.88
£978.94 average per person
Total £1,957.88
£1,017.44 average per person
Total £2,034.88
£1,028.94 average per person
Total £2,057.88
£1,028.94 average per person
Total £2,057.88
£1,032.13 average per person
Total £2,064.26
£1,032.56 average per person
Total £2,065.12
£1,051.94 average per person
Total £2,103.88

Sofitel Chicago Water Tower

4 stars

0.2 miles Northwest from the centre of Chicago map

Reviewer score 4.6 / 5 104 reviews
£990.97 average per person
Total £1,981.93
£990.97 average per person
Total £1,981.93
£990.97 average per person
Total £1,981.93
£990.97 average per person
Total £1,981.93
£1,029.47 average per person
Total £2,058.93
£1,040.97 average per person
Total £2,081.93
£1,040.97 average per person
Total £2,081.93
£1,044.16 average per person
Total £2,088.31
£1,044.59 average per person
Total £2,089.17
£1,063.97 average per person
Total £2,127.93

Ramada Lake Shore Chicago

2 stars

6.6 miles South from the centre of Chicago map

Reviewer score 2.9 / 5 88 reviews
£837.84 average per person
Total £1,675.68
£837.84 average per person
Total £1,675.68
£837.84 average per person
Total £1,675.68
£837.84 average per person
Total £1,675.68
£876.34 average per person
Total £1,752.68
£887.84 average per person
Total £1,775.68
£887.84 average per person
Total £1,775.68
£891.03 average per person
Total £1,782.06
£891.46 average per person
Total £1,782.92
£910.84 average per person
Total £1,821.68

Central Loop Hotel

3 stars

1.2 miles South from the centre of Chicago map

Reviewer score 4.1 / 5 253 reviews
Special Promotion
  • EXCLUSIVE! Save 10% on this stay

View all available promotions

£865.86 average per person
Total £1,731.71
£865.86 average per person
Total £1,731.71
£865.86 average per person
Total £1,731.71
£865.86 average per person
Total £1,731.71
£904.36 average per person
Total £1,808.71
£915.86 average per person
Total £1,831.71
£915.86 average per person
Total £1,831.71
£919.05 average per person
Total £1,838.09
£919.48 average per person
Total £1,838.95
£938.86 average per person
Total £1,877.71

Swissotel Chicago

4 stars

0.6 miles Southeast from the centre of Chicago map

Reviewer score 4.1 / 5 226 reviews
£1,023.43 average per person
Total £2,046.86
£1,023.43 average per person
Total £2,046.86
£1,023.43 average per person
Total £2,046.86
£1,023.43 average per person
Total £2,046.86
£1,061.93 average per person
Total £2,123.86
£1,073.43 average per person
Total £2,146.86
£1,073.43 average per person
Total £2,146.86
£1,076.62 average per person
Total £2,153.24
£1,077.05 average per person
Total £2,154.10
£1,096.43 average per person
Total £2,192.86

Code share information

Departure Thu, 12 Jul
Flight 929
Return Tue, 17 Jul
Flight 922
Flight 922

Code share information

Departure Thu, 12 Jul
Flight 929
Return Tue, 17 Jul
Flight 9357
Operated by United Airlines

Code share information

Departure Thu, 12 Jul
Flight 929
Return Tue, 17 Jul
Flight 9357
Operated by United Airlines

Code share information

Departure Thu, 12 Jul
Flight 929
Return Tue, 17 Jul
Flight 520
Flight 864

Code share information

Departure Thu, 12 Jul
Flight 39
Return Tue, 17 Jul
Flight 40

Code share information

Departure Thu, 12 Jul
Flight 99
Return Tue, 17 Jul
Flight 90

Code share information

Departure Thu, 12 Jul
Flight 1540
Operated by American Airlines
Return Tue, 17 Jul
Flight 1541
Operated by American Airlines

Code share information

Departure Thu, 12 Jul
Flight 19
Flight 1493
Return Tue, 17 Jul
Flight 1564
Flight 56

Code share information

Departure Thu, 12 Jul
Flight 6079
Operated by Delta Air Lines
Flight 5938
Operated by Delta Air Lines
Return Tue, 17 Jul
Flight 6860
Operated by Delta Air Lines
Flight 6078
Operated by Delta Air Lines

Code share information

Departure Thu, 12 Jul
Flight 4217
Operated by American Airlines
Return Tue, 17 Jul
Flight 4212
Operated by American Airlines
1

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 41min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:26
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 9hr 55min
Depart
06:00
Chicago, Illinois , United States
O'Hare Airport (ORD) Terminal TERMINAL 1
Stop 1
08:45
Washington DC, District of Columbia , United States
Dulles Airport (IAD) Terminal TERMINAL

This stop is a connection to a new plane with the same flight number.

Change planes. Layover: 0hr 54min

Stops: 1

Depart
09:39
Washington DC, District of Columbia , United States
Dulles Airport (IAD) Terminal TERMINAL
Arrive
21:55
London , United Kingdom
Heathrow Airport (LHR) Terminal TERMINAL 1
2

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 41min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:26
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 8hr 5min
Depart
15:50
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
05:55
London , United Kingdom
Heathrow Airport (LHR)

Flight 9357 Operated by United Airlines

This is an overnight flight.

3

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 41min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:26
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 8hr 5min
Depart
15:50
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
05:55
London , United Kingdom
Heathrow Airport (LHR)

Flight 9357 Operated by United Airlines

This is an overnight flight.

4

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 41min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:26
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 9hr 45min
Depart
15:45
Chicago, Illinois , United States
O'Hare Airport (ORD)
Stop 1
18:44
Montreal, Quebec , Canada
Pierre Elliott Trudeau Airport (YUL)

Change planes. Layover: 0hr 56min

Depart
19:40
Montreal, Quebec , Canada
Pierre Elliott Trudeau Airport (YUL)
Arrive
07:30
London , United Kingdom
Heathrow Airport (LHR)

This is an overnight flight.

5

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 55min
Depart
11:00
London , United Kingdom
Heathrow Airport (LHR)
Arrive
13:55
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 8hr 0min
Depart
18:00
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
08:00
London , United Kingdom
Heathrow Airport (LHR)

This is an overnight flight.

6

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 25min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:10
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 7hr 35min
Depart
09:10
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
22:45
London , United Kingdom
Heathrow Airport (LHR)
7

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 25min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:10
Chicago, Illinois , United States
O'Hare Airport (ORD)

Flight 1540 Operated by American Airlines

Return
Tue, 17 Jul
Total time: 7hr 35min
Depart
09:10
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
22:45
London , United Kingdom
Heathrow Airport (LHR)

Flight 1541 Operated by American Airlines

8

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 12hr 40min
Depart
09:05
London , United Kingdom
Heathrow Airport (LHR)
Stop 1
12:30
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)

Change planes. Layover: 2hr 52min

Depart
15:22
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)
Arrive
15:45
Chicago, Illinois , United States
O'Hare Airport (ORD)
Return
Tue, 17 Jul
Total time: 11hr 30min
Depart
14:00
Chicago, Illinois , United States
O'Hare Airport (ORD)
Stop 1
16:23
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)

Change planes. Layover: 2hr 22min

Depart
18:45
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)
Arrive
07:30
London , United Kingdom
Heathrow Airport (LHR)

This is an overnight flight.

9

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 12hr 47min
Depart
09:05
London , United Kingdom
Heathrow Airport (LHR)
Stop 1
12:30
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)

Flight 6079 Operated by Delta Air Lines

Change planes. Layover: 3hr 10min

Depart
15:40
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)
Arrive
15:52
Chicago, Illinois , United States
Midway Airport (MDW)

Flight 5938 Operated by Delta Air Lines

Return
Tue, 17 Jul
Total time: 10hr 35min
Depart
18:30
Chicago, Illinois , United States
Midway Airport (MDW)
Stop 1
20:48
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)

Flight 6860 Operated by Delta Air Lines

Change planes. Layover: 1hr 32min

Depart
22:20
Detroit, Michigan , United States
Detroit Wayne County Airport (DTW)
Arrive
11:05
London , United Kingdom
Heathrow Airport (LHR)

Flight 6078 Operated by Delta Air Lines

This is an overnight flight.

10

Note: You may switch your flight after selecting a package.

Leave
Thu, 12 Jul
Total time: 8hr 25min
Depart
07:45
London , United Kingdom
Heathrow Airport (LHR)
Arrive
10:10
Chicago, Illinois , United States
O'Hare Airport (ORD)

Flight 4217 Operated by American Airlines

Return
Tue, 17 Jul
Total time: 7hr 35min
Depart
09:10
Chicago, Illinois , United States
O'Hare Airport (ORD)
Arrive
22:45
London , United Kingdom
Heathrow Airport (LHR)

Flight 4212 Operated by American Airlines

11