Cheap Vacations in Chicago

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Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Chicago - Alsip

Red Roof Inn Chicago - Alsip

2.5 out of 5
Price was $266, price is now $221 per person
$221
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (MDW)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $637, price is now $419 per person
$419
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $348, price is now $252 per person
$252
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Best Western River North Hotel

Best Western River North Hotel

2.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $372, price is now $270 per person
$270
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $368, price is now $276 per person
$276
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Comfort Suites near I-80 and I-94

Comfort Suites near I-80 and I-94

2.5 out of 5
Price was $368, price is now $293 per person
$293
per person
Feb 7 - Feb 10
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Price was $300, price is now $242 per person
$242
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $332, price is now $270 per person
$270
per person
Jan 30 - Feb 1
found 2 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was $306, price is now $249 per person
$249
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Downtown Chicago
Price was $297, price is now $243 per person
$243
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)

3-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Motel 6 Rockford, IL – RFD Airport

Motel 6 Rockford, IL – RFD Airport

2 out of 5
Price was $253, price is now $202 per person
$202
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Rockford (RFD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $637, price is now $419 per person
$419
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Destination Geneva National

Destination Geneva National

4 out of 5
Save 100% on your flight
Price was $359, price is now $243 per person
$243
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Lodge Geneva National

Lodge Geneva National

4 out of 5
Price was $331, price is now $237 per person
$237
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $638, price is now $460 per person
$460
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Comfort Suites near I-80 and I-94

Comfort Suites near I-80 and I-94

2.5 out of 5
Price was $368, price is now $293 per person
$293
per person
Feb 7 - Feb 10
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Price was $435, price is now $349 per person
$349
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Quality Inn Bolingbrook I-55

Quality Inn Bolingbrook I-55

2.5 out of 5
Price was $287, price is now $233 per person
$233
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,129, price is now $920 per person
$920
per person
Feb 7 - Feb 10
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Price was $590, price is now $482 per person
$482
per person
Feb 13 - Feb 16
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $521, price is now $427 per person
$427
per person
Jan 29 - Feb 1
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Price was $537, price is now $442 per person
$442
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)

4-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $421, price is now $319 per person
$319
per person
Feb 7 - Feb 11
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was $550, price is now $435 per person
$435
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Price was $914, price is now $739 per person
$739
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was $493, price is now $402 per person
$402
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Westin Chicago River North

The Westin Chicago River North

4.5 out of 5
Price was $725, price is now $610 per person
$610
per person
Feb 7 - Feb 11
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was $524, price is now $441 per person
$441
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Motel 6 Joliet, IL - Chicago - I-55

Motel 6 Joliet, IL - Chicago - I-55

2 out of 5
Price was $408, price is now $346 per person
$346
per person
Feb 7 - Feb 11
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (CHI)
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
Price was $556, price is now $474 per person
$474
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Price was $431, price is now $368 per person
$368
per person
Jan 19 - Jan 23
found 14 hours ago
Roundtrip flight included
Fort Myers (RSW) to Chicago (ORD)
Wyndham Garden Elk Grove Village/O'Hare

Wyndham Garden Elk Grove Village/O'Hare

3 out of 5
Price was $537, price is now $464 per person
$464
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Price was $582, price is now $503 per person
$503
per person
Feb 7 - Feb 11
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was $449, price is now $390 per person
$390
per person
Jan 21 - Jan 25
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

5-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
Price was $541, price is now $311 per person
$311
per person
Feb 10 - Feb 15
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $768, price is now $432 per person
$432
per person
Feb 10 - Feb 15
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $785, price is now $442 per person
$442
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $647, price is now $375 per person
$375
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $630, price is now $382 per person
$382
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $702, price is now $427 per person
$427
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $617, price is now $378 per person
$378
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $632, price is now $390 per person
$390
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $584, price is now $368 per person
$368
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $657, price is now $417 per person
$417
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,596, price is now $1,014 per person
$1,014
per person
Feb 10 - Feb 15
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $657, price is now $420 per person
$420
per person
Feb 8 - Feb 13
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)

Flight deals to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 14 - Sat, Jan 17
ATL
Atlanta
ORD
Chicago
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jan 14 from Atlanta to Chicago, returning Sat, Jan 17, priced at $68 found 3 days ago
Fri, Jan 16 - Mon, Jan 19
JFK
New York
ORD
Chicago
$70 Roundtrip, found 17 hours ago
$70
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Jan 16 from New York to Chicago, returning Mon, Jan 19, priced at $70 found 17 hours ago
Thu, Jan 15 - Sat, Jan 17
LGA
New York
ORD
Chicago
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jan 15 from New York to Chicago, returning Sat, Jan 17, priced at $82 just found

Top rated hotels for your Chicago vacation

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at Hilton Chicago/Magnificent Mile Suites, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake Michigan.
Pet friendly
Free WiFi
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.12 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown is in the heart of Chicago, within a 5-minute walk of Millennium Park and CIBC Theatre.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$88 nightly
The price is $103 total per night
$103 total
Dec 28 - Dec 29
Total with taxes and fees
With a stay at Club Quarters Hotel Wacker at Michigan, Chicago, you'll be centrally located in Chicago, steps from Chicago Riverwalk and 5 minutes by foot from Michigan Avenue.
Pet friendly
Free WiFi
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Lowest 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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com 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.