Cheap Vacations in Chicago

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Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Downtown Chicago
Price was $277, price is now $204 per person
$204
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $533, price is now $388 per person
$388
per person
Jan 15 - Jan 18
found 3 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was $340, price is now $254 per person
$254
per person
Jan 23 - Jan 25
just found
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was $488, price is now $366 per person
$366
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was $334, price is now $252 per person
$252
per person
Jan 23 - Jan 25
just found
Roundtrip flight included
Mesa (AZA) 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 $380, price is now $286 per person
$286
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 $279 per person
$279
per person
Jan 23 - Jan 25
just found
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was $451, price is now $349 per person
$349
per person
Jan 18 - Jan 21
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $350, price is now $272 per person
$272
per person
Jan 23 - Jan 25
just found
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $296, price is now $230 per person
$230
per person
Jan 23 - Jan 25
just found
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)

3-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $249, price is now $179 per person
$179
per person
Jan 16 - Jan 19
found 12 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $796, price is now $535 per person
$535
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $331, price is now $223 per person
$223
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $269, price is now $189 per person
$189
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Price was $353, price is now $256 per person
$256
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $533, price is now $388 per person
$388
per person
Jan 15 - Jan 18
found 3 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Price was $277, price is now $204 per person
$204
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Price was $300, price is now $225 per person
$225
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $537, price is now $403 per person
$403
per person
Jan 18 - Jan 21
found 12 hours ago
Roundtrip flight included
Dallas (DAL) 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 $380, price is now $286 per person
$286
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $449, price is now $344 per person
$344
per person
Jan 18 - Jan 21
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Price was $451, price is now $349 per person
$349
per person
Jan 18 - Jan 21
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

4-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was $314, price is now $220 per person
$220
per person
Jan 22 - Jan 26
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $487, price is now $331 per person
$331
per person
Jan 22 - Jan 26
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,177, price is now $818 per person
$818
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $673, price is now $475 per person
$475
per person
Jan 22 - Jan 26
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $632, price is now $454 per person
$454
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $382, price is now $275 per person
$275
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $592, price is now $426 per person
$426
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $513, price is now $372 per person
$372
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $513, price is now $373 per person
$373
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) 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 $518, price is now $389 per person
$389
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $492, price is now $371 per person
$371
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Price was $564, price is now $427 per person
$427
per person
Jan 31 - Feb 4
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

5-night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Price was $400, price is now $309 per person
$309
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was $488, price is now $366 per person
$366
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Price was $647, price is now $488 per person
$488
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $686, price is now $519 per person
$519
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $612, price is now $464 per person
$464
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
Price was $448, price is now $340 per person
$340
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
Price was $882, price is now $670 per person
$670
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $810, price is now $627 per person
$627
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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 $566, price is now $442 per person
$442
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
Chicago Marriott Oak Brook

Chicago Marriott Oak Brook

3.5 out of 5
Price was $576, price is now $457 per person
$457
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $607, price is now $485 per person
$485
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
Courtyard by Marriott Chicago Glenview/Northbrook

Courtyard by Marriott Chicago Glenview/Northbrook

3.5 out of 5
Price was $463, price is now $372 per person
$372
per person
Feb 5 - Feb 10
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

6-7 night Chicago vacations

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was $644, price is now $485 per person
$485
per person
Jan 21 - Jan 28
found 1 day 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
Save 100% on your flight
Price was $1,510, price is now $996 per person
$996
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was $857, price is now $601 per person
$601
per person
Jan 21 - Jan 28
found 1 day 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 $1,003, price is now $707 per person
$707
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was $707, price is now $521 per person
$521
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
Price was $840, price is now $627 per person
$627
per person
Jan 21 - Jan 28
found 1 day 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 $801, price is now $603 per person
$603
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
DoubleTree by Hilton Chicago - Oak Brook

DoubleTree by Hilton Chicago - Oak Brook

4 out of 5
Price was $746, price is now $572 per person
$572
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

3 out of 5
Price was $748, price is now $577 per person
$577
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Four Points by Sheraton Chicago Schaumburg

Four Points by Sheraton Chicago Schaumburg

3 out of 5
Price was $704, price is now $545 per person
$545
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Crowne Plaza Lombard Downers Grove by IHG

Crowne Plaza Lombard Downers Grove by IHG

3.5 out of 5
Price was $841, price is now $652 per person
$652
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Holiday Inn Express Chicago NW - Arlington Heights by IHG

Holiday Inn Express Chicago NW - Arlington Heights by IHG

2.5 out of 5
Price was $653, price is now $507 per person
$507
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)

Flight deals to Chicago

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

Thu, Jan 29 - Sun, Feb 1
EWR
New York
ORD
Chicago
$72 Roundtrip, found 3 days ago
$72
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from New York to Chicago, returning Sun, Feb 1, priced at $72 found 3 days ago
Wed, Jan 21 - Fri, Jan 23
ATL
Atlanta
ORD
Chicago
$78 Roundtrip, found 5 days ago
$78
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Atlanta to Chicago, returning Fri, Jan 23, priced at $78 found 5 days ago
Fri, Jan 23 - Sun, Jan 25
JFK
New York
ORD
Chicago
$80 Roundtrip, found 11 hours ago
$80
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, Jan 23 from New York to Chicago, returning Sun, Jan 25, priced at $80 found 11 hours ago

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
$81 nightly
The price is $95 total per night
$95 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 17 - Dec 18
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.